Insecticidal amides with nitrogen-containing benzo-Fused bicyclic ring systems

ABSTRACT

Disclosed are compounds of Formula I and compounds of Formula II (including all geometric and stereoisomers), N-oxides thereof and salts thereof, certain compositions comprising the compounds of Formula I and/or the compounds of Formula II and certain uses of those compounds and compositions for controlling invertebrate pests INSERT FORMULA I AND II HERE wherein A, B, J, R 1 , R 2 , R 3 , R 4 , M, M 1  and n are as defined in the disclosure.

FIELD OF THE INVENTION

This invention relates to certain indoline carboxamides and thiamides, their N-oxides, suitable salts and compositions, and a method of their use for controlling invertebrate pests in both agronomic and nonagronomic environments.

BACKGROUND OF THE INVENTION

The control of invertebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action.

EP919542 discloses phthalic diamides of Formula i as insecticides

wherein, among others, Z¹ and Z² are O or S; and R¹, R² and R³ are, among others, H, alkyl or substituted alkyl.

WO 96/23783 and U.S. Pat. No. 5,514,690 disclose indoline carboxamide derivatives as pharmaceutical agents.

SUMMARY OF THE INVENTION

This invention is related to compounds of Formula I and compounds of Formula II including all geometric and stereoisomers, N-oxides and salts thereof:

wherein

-   -   each J is independently a phenyl ring or a 5- or 6-membered         heteroaromatic ring, each ring substituted with 1 to 4 R⁵;     -   A and B are independently O or S;     -   n is 0, 1, 2 or 3;     -   R¹ is H, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆         alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl; or     -   R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆         cycloalkyl each optionally substituted with one or more         substituents selected from the group consisting of halogen, CN,         NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄         alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄         alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino;     -   R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆         cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino,         C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆         alkylcarbonyl;     -   R³ is H; or     -   R³ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆         cycloalkyl each optionally substituted with one or more         substituents selected from the group consisting of halogen, CN,         NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl         and C₁-C₄ alkylsulfonyl; or     -   R² and R³ can be taken together with the nitrogen to which they         are attached to form a ring containing 2 to 6 atoms of carbon         and optionally one additional atom of nitrogen, sulfur or         oxygen, said ring may be optionally substituted with 1 to 4         substituents selected from the group consisting of C₁-C₂ alkyl,         halogen, CN, NO₂ and C₁-C₂ alkoxy; and     -   each R⁴ and each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆         alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆         haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen,         CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,         C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,         C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino,         C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆         alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, or C₃-C₆         trialkylsilyl; or     -   each R⁴ and each R⁵ is independently a phenyl, benzyl, phenoxy,         or 5- or 6-membered heteroaromatic ring, each ring optionally         substituted with one to three substituents independently         selected from the group consisting of C₁-C₄ alkyl, C₂-C₄         alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen,         CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄         alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈         dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆         (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆         alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈         dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or     -   two R⁵ groups when attached to adjacent carbon atoms can be         taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—;     -   M and M¹ are each independently CR⁶R⁷, NR⁸, O or S when the bond         between M and M¹ is a single bond; and are each independently         CR⁶ or N when the bond between M and M¹ is an aromatic bond;     -   each R⁶ and each R⁷ is independently H, C₁-C₄ alkyl, halogen,         CN, C₁-C₄ haloalkyl or C₁-C₄ alkoxy; and     -   each R⁸ is independently H or C₁-C₄ alkyl.

This invention provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof (e.g., as a composition described herein).

Of note is a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I or a compound of Formula II (e.g., as a composition described herein).

This invention also provides a composition comprising at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent; and provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said composition.

Of note is a composition for controlling an invertebrate pest comprising (1) at least one compound selected from the group consisting of compounds of Formula I and compounds of Formula II, and (2) at least one additional compound or agent for controlling invertebrate pests; and provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment a biologically effective amount of said composition.

This invention also provides a compound of Formula II, an N-oxide or a salt thereof; a composition which comprises at least one compound of Formula II, an N-oxide or salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and a method for controlling at least one invertebrate pest which comprises contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) or with a biologically effective amount of said composition.

Of note are compounds of Formula II: compositions for controlling an invertebrate pest which comprise at least one compound of Formula II and at least one additional component selected from the group consisting of surfactants, solid diluents, liquid diluents diluents and other biologically active compounds and agents; and methods for controlling an invertebrate pest which comprise contacting the invertebrate pest or its environment a biologically effective amount of said compounds or said compositions.

Of note are compounds of Formula Ic

-   -   wherein     -   M and M¹ are each independently CR⁶R⁷, NR⁸, O or S when the bond         between M and M¹ is a single bond, provided that M and M¹ are         not both CR⁶R⁷; and are each independently CR⁶ or N when the         bond between M and M¹ is an aromatic bond; and     -   A, B, J, R¹ through R⁴, R⁶ through R⁸ and n are defined as         above.

This invention also provides compounds of Formula Id

-   -   wherein each R⁴ and each R⁵ is independently H, C₁-C₆ alkyl,         C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl,         C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl,         halogen, CN, C₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄         haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄         alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl,         C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino,         C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆         alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈         dialkylaminocarbonyl, or C₃-C₆ trialkylsilyl; or     -   each R⁵ is independently a phenyl, benzyl, phenoxy, or 5- or         6-membered heteroaromatic ring, each ring optionally substituted         with one to three substituents independently selected from the         group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,         C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄         haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄         alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,         C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆         cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄         alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,         C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or     -   two R⁵ groups when attached to adjacent carbon atoms can be         taken together as —OCF₂O—, —CF₂CF₂O—or —OCF₂CF₂O—; and     -   A, B, J, R¹ through R³, R⁶ through R⁸ and n are defined as         above.

This invention also provides a composition which comprises at least one compound of Formula Id, an N-oxide or a salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and a method for controlling at least one invertebrate pest which comprises contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) or with a biologically effective amount of said composition.

DETAILS OF THE INVENTION

In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH₃S(O), CH₃CH₂S(O), CH₃CH₂CH₂S(O), (CH₃)₂CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH₃S(O)₂, CH₃CH₂S(O)₂, CH₃CH₂CH₂S(O)₂, (CH₃)₂CHS(O)₂ and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. “Alkylamino” includes branched or straight-chain alkylamino moieties such as methylamino, ethylamino, and the different propylamino, butylamino, pentylamino and hexylamino isomers. Examples of“alkylcarbonyl” include C(O)CH₃, C(O)CH₂CH₂CH₃ and C(O)CH(CH₃)₂. Examples of “alkoxycarbonyl” include CH₃OC(═O), CH₃CH₂OC(═O), CH₃CH₂CH₂OC(═O), (CH₃)₂CHOC(═O) and the different butoxy- or pentoxycarbonyl isomers. Examples of “alkylaminocarbonyl” include CH₃NHC(═O), CH₃CH₂NHC(═O), CH₃CH₂CH₂NHC(═O), (CH₃)₂CHNHC(═O) and the different butylamino- or pentylaminocarbonyl isomers. The term “dialkylamino” includes amino functions substituted with two alkyl groups that may be the same or different. “Dialkylaminocarbonyl” is defined analogously, and examples include (CH₃)₂NC(═O) and CH₃CH₂NCH₃C(═O).

The term “cycloalkyl”, used either alone or in compound words such as “cycloalkylamino” or “halocycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term “heteroaromatic ring” denotes fully aromatic rings in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs (where aromatic indicates that the Hückel rule is satisfied). The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen.

The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂ and CF₃CH₂CH═CHCH₂. Examples of “haloalkynyl” include HC≡CCHCl, CF₃C≡C, CCl₃C≡C and FCH₂C≡CCH₂. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O, HCF₂CH₂CH₂O and CF₃CH₂O. Examples of “haloalkylthio” include CCl₃S, CF₃S, CCl₃CH₂S and ClCH₂CH₂CH₂S. Examples of “haloalkylsulfinyl” include CF₃S(O), CCl₃S(O), CF₃CH₂S(O) and CF₃CF₂S(O). Examples of “haloalkylsulfonyl” include CF₃S(O)₂, CCl₃S(O)₂, CF₃CH₂S(O)₂ and CF₃CF₂S(O)₂.

The combination of a broken line and an unbroken line between M and M¹ as shown in Formula I and Formula II designates that the bond between M and M¹ can be either a single bond or an aromatic bond. When the bond between M and M¹ is an aromatic bond then M, M¹ and the bond between them form a portion of an aromatic ring. For example, when the bond between M and M¹ is a single bond and M and M¹ are both CR⁶R⁷, then M and M¹ are both within an indoline ring system; and when the bond between M and M¹ is an aromatic bond and M and M¹ are both CR⁶, then M and M¹ are both within an indole ring system.

The total number of carbon atoms in a substituent group is indicated by the “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 8. For example, C₁-C₃ alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyl designates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄ alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. In the above recitations, when a compound of Formula I contains a heteroaromatic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

When a group contains a substituent which can be hydrogen, for example R³, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When the number of optional substituents on a group is 0, for example when n is 0, then it is recognized that this is equivalent to said group being unsubstituted. When a bond is depicted as floating, the substituent may be attached to any of the available carbons on the ring by replacement of hydrogen. When R² and R³ are taken together with the nitrogen to which they are attached to form a ring, said ring can be optionally substituted on any available carbon or optionally nitrogen in said ring.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention can be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

The present invention involves compounds selected from Formula I or Formula II, N-oxides and salts thereof. One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. In the compositions and methods of this invention, the salts of the compounds of the invention are preferably suitable for the agronomic and/or non-agronomic uses described herein.

As noted above, this invention includes a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of at least one of a compound selected from the group consisting a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or salt thereof. Preferred methods for reasons including greater control of invertebrate pests and/or ease of compound synthesis are:

Preferred 1. The method comprising applying a biologically effective amount of a compound of Formula I wherein

-   -   A and B are both O;     -   R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and     -   n is 0, 1 or 2.

Preferred 2. The method comprising applying a biologically effective amount of a compound of Formula II wherein

-   -   A and B are both O;     -   R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and     -   n is 0, 1 or 2.

Preferred 3. The method of Preferred 1 or Preferred 2 comprising applying a biologically effective amount of a compound of Formula I or a compound of Formula II wherein

-   -   J is a phenyl ring or a 5- or 6-membered heteroaromatic ring         selected from the group consisting of J-1, J-2, J-3 and J-4     -   Q is O, S or NR⁵;     -   W, X, Y and Z are independently N or CR⁵, provided that in J-3         and J-4 at least one of the group consisting of W, X, Y and Z is         N;     -   R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;     -   R³ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alknyl or C₃-C₆         cycloalkyl each optionally substituted with one or more         substituents selected from the group consisting of halogen, CN,         C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂         alkylsulfonyl;     -   each R⁴ is independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen,         CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄         alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄         haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;     -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₆ haloalkyl,         halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄         alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl         or C₂-C₄ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈         dialkylaminocarbonyl; or     -   each R⁵ is independently a phenyl, benzyl or a 5- or 6-membered         heteroaromatic ring, each ring optionally substituted with C₁-C₄         alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆         halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄         haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄         alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆         cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄         alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,         C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or     -   two R⁵ groups when attached to adjacent carbon atoms can be         taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—.

Preferred 4. The method of Preferred 3 comprising applying a biologically effective amount of a compound of Formula I wherein

-   -   R¹ is H or C₁-C₄ alkyl;     -   R² is H or C₁-C₄ alkyl;     -   R³ is H, C₁-C₄ alkyl optionally substituted with halogen, CN,         OCH₃, or S(O)_(p)CH₃;     -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,         halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄         alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,         C₂-C₄ alkoxycarbonyl or C₃-C₈ dialkylaminocarbonyl; or a phenyl,         benzyl, or a 5- or 6-membered heteroaromatic ring, each ring         optionally substituted with halogen, CN, NO₂, C₁-C₄ alkyl, C₂-C₄         alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₁-C₄         alkoxy or C₁-C₄ haloalkoxy;     -   provided that at least one R⁵ is other than H and is attached to         J at the position ortho to the N(R¹)C(═B) moiety; and     -   p is 0, 1 or 2.

Preferred 5. The method of Preferred 4 comprising applying a biologically effective amount of a compound of Formula I wherein

-   -   J is a substituted phenyl, a substituted pyrazole, a substituted         pyrrole, a substituted pyridine or a substituted pyrimidine.

Preferred 6. The method of Preferred 5 comprising applying a biologically effective amount of a compound of Formula I wherein

-   -   R¹ and R² are each H.

Preferred 7. The method of Preferred 3 comprising applying a biologically effective amount of a compound of Formula II wherein

-   -   R² is H;     -   R³ is C₁-C₄ alkyl; and     -   at least one R⁵ is other than H and is attached to J at the         position ortho to the N(R¹)C(═B) moiety.

As noted above, this invention also provides compounds of Formula Id. Preferred compounds for ease of synthesis and/or greater control of invertebrate pests are:

Preferred 8. Compounds of Formula Id wherein

-   -   A and B are both O;     -   R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;     -   n is 0, 1 or 2.

Preferred 9. Compounds of Preferred 8 wherein

-   -   J is a phenyl ring or a 5- or 6-membered heteroaromatic ring         selected from the group consisting of J-1, J-2, J-3 and J-4     -   Q is O, S or NR⁵;     -   W, X, Y and Z are independently N or CR⁵, provided that in J-3         and J-4 at least one of the group consisting of W, X, Y and Z is         N;     -   R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;     -   R³ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆         cycloalkyl each optionally substituted with one or more         substituents selected from the group consisting of halogen, CN,         C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂         alkylsulfonyl;     -   each R⁴ is independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen,         CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄         alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄         haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;     -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₆ haloalkyl,         halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄         alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl         or C₂-C₄ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈         dialkylaminocarbonyl; or     -   each R⁵ is independently a phenyl, benzyl or a 5- or 6-membered         heteroaromatic ring, each ring optionally substituted with C₁-C₄         alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆         halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄         haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄         alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆         cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄         alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,         C₃-C8 dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or     -   two R⁵ groups when attached to adjacent carbon atoms can be         taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—.

Preferred 10. Compounds of Preferred 9 wherein

-   -   R¹ is H or C₁-C₄ alkyl;     -   R² is H or C₁-C₄ alkyl;     -   R³ is H, C₁-C₄ alkyl optionally substituted with halogen, CN,         OCH₃, or S(O)_(p)CH₃;     -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,         halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄         alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,         C₂-C₄ alkoxycarbonyl or C₃-C₈ dialkylaminocarbonyl; or a phenyl,         benzyl, or a 5- or 6-memnbered heteroaromatic ring, each ring         optionally substituted with halogen, CN, NO₂, C₁-C₄ alkyl, C₂-C₄         alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₁-C₄         alkoxy or C₁-C₄ haloalkoxy;     -   provided that at least one R⁵ is other than H and is attached to         J at the position ortho to the N(R¹)C(═B) moiety; and     -   p is 0, 1 or 2.

Preferred 1 1. Compounds of Preferred 10 wherein

-   -   J is a substituted phenyl, a substituted pyrazole, a substituted         pyrrole, a substituted pyridine or a substituted pyrimidine.

Preferred 12. Compounds of Preferred 11 wherein R¹ and R² are each H.

Of note are compounds of Formula Ic. Preferred compounds of Formula Ic for ease of synthesis and/or greater control of invertebrate pests are:

Preferred 8a. Compounds of Formula Ic wherein

-   -   A and B are both O;     -   R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and     -   n is 0, 1 or 2.

Preferred 9a. Compounds of Preferred 8a wherein

-   -   J is a phenyl ring or a 5- or 6-membered heteroaromatic ring         selected from the group consisting of J-1, J-2, J-3 and J-4     -   Q is O, S or NR⁵;     -   W, X, Y and Z are independently N or CR⁵, provided that in J-3         and J-4 at least one of the group consisting of W, X, Y and Z is         N;     -   R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;     -   R³ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆         cycloalkyl each optionally substituted with one or more         substituents selected from the group consisting of halogen, CN,         C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂         alkylsulfonyl;     -   each R⁴ is independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen,         CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄         alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄         haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;     -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₆ haloalkyl,         halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄         alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl         or C₂-C₄ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈         dialkylaminocarbonyl; or     -   each R⁵ is independently a phenyl, benzyl or a 5- or 6-mernbered         heteroaromatic ring, each ring optionally substituted with C₁-C₄         alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆         halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄         haloalkoxy, C₁-C₄ alkyldiio, C₁-C₄ alkylsulfinyl, C₁-C₄         alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆         cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄         alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,         C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or     -   two R⁵ groups when attached to adjacent carbon atoms can be         taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—.

Preferred 10a. Compounds of Preferred 9a wherein

-   -   R¹ is H or C₁-C₄ alkyl;     -   R² is H or C₁-C₄ alkyl;     -   R³ is H, C₁-C₄ alkyl optionally substituted with halogen, CN,         OCH₃, or S(O)_(p)CH₃;     -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,         halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄         alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl,         C₂-C₄ alkoxycarbonyl or C₃-C₈ dialkylaminocarbonyl; or a phenyl,         benzyl, or a 5- or 6-membered heteroaromatic ring, each ring         optionally substituted with halogen, CN, NO₂, C₁-C₄ alkyl, C₂-C₄         alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₁-C₄         alkoxy or C₁-C₄ haloalkoxy;     -   provided that at least one R⁵ is other than H and is attached to         J at the position ortho to the N(R¹)C(═B) moiety; and     -   p is 0, 1 or 2.

Preferred 11a. Compounds of Preferred 10a wherein

-   -   J is a substituted phenyl, a substituted pyrazole, a substituted         pyrrole, a substituted pyridine or a substituted pyrimidine.

Preferred 12a. Compounds of Preferred 11a wherein R¹ and R² are each H.

As noted above, this invention also provides compounds of Formula II. Preferred compounds for ease of synthesis and/or greater control of invertebrate pests are:

Preferred 13. Compounds of Formula II wherein

-   -   A and B are both O;     -   R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and     -   n is 0, or 2.

Preferred 14. Compounds of Preferred 13 wherein

-   -   J is a phenyl ring or a 5- or 6-membered heteroaromatic ring         selected from the group consisting of J-1, J-2, J-3 and J-4     -   Q is O, S or NR⁵;     -   W, X, Y and Z are independently N or CR⁵, provided that in J-3         and J4 at least one of the group consisting of W, X, Y and Z is         N;     -   R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆         cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;     -   R³ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆         cycloalkyl each optionally substituted with one or more         substituents selected from the group consisting of halogen, CN,         C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂         alkylsulfonyl;     -   each R⁴ is independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen,         CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄         alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄         haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;     -   each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₆ haloalkyl,         halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄         alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄         haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl         or C₂-C₄ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈         dialkylaminocarbonyl; or     -   each R⁵ is independently a phenyl, benzyl or a 5- or 6-membered         heteroaromatic ring, each ring optionally substituted with C₁-C₄         alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆         halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄         haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄         alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆         cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄         alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,         C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or     -   two R⁵ groups when attached to adjacent carbon atoms can be         taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—.

Preferred 15. Compounds of Formula II of Preferred 14 wherein

-   -   R² is H;     -   R³ is C₁-C₄ alkyl; and     -   at least one R⁵ is other than H and is attached to J at the         position ortho to the N(R¹)C(═B) moiety.

This invention also provides a composition comprising at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent; and also provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said composition. Preferred compositions include compositions wherein the at least one compound of Formula I, an N-oxide or a salt thereof and/or Formula II, an N-oxide or a salt thereof is selected from the compounds in Preferred 1 through 7. Also preferred is a composition further comprising an additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.

Of note are compositions for controlling an invertebrate pest comprising (1) at least one compound selected from the group consisting of compounds of Formula I and compounds of Formula II, and (2) at least one additional compound or agent for controlling invertebrate pests; and also provides a method for controlling an invertebrate pest comprising the invertebrate pest or its environment a biologically effective amount of said composition. Preferred compositions include compositions wherein component (1) is selected from compounds(s) of Formula I and/or Formula II as preferred for the preferred method in Preferred 1 through 7.

This invention also provides a composition comprising at least one compound of Formula II, an N-oxide or a salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and also provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) of Formula II, its N-oxides and salts thereof or with a biologically effective amount of said composition. Preferred compositions and methods include compositions and methods wherein the at least one compound of Formula II, an N-oxides or a salt thereof, is selected from the compounds in Preferred 13 through 15.

Of note is a composition for controlling an invertebrate pest comprising at least one compound of Formula II and at least one additional component selected from the group consisting of surfactants, solid diluents, liquid diluents and other biologically active compounds and agents; and also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment a biologically effective amount of said composition. Preferred compositions include compositions wherein the compound(s) of Formula II, are selected from the compounds preferred in Preferred 13 through 15.

This invention also provides a composition comprising at least one compound of Formula Id, an N-oxide or a salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and also provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) or with a biologically effective amount of said composition. Preferred compositions and methods include compositions and methods wherein the at least one compound of Formula Id, a N-oxide or a salt thereof, is selected from the compounds in Preferred 8 through 12.

Of note is a composition for controlling an invertebrate pest comprising at least one compound of Formula Ic and at least one additional component selected from the group consisting of surfactants, solid diluents, liquid diluents and other biologically active compounds or agents; and also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment a biologically effective amount of said composition. Preferred compositions include compositions wherein the compound(s) of Formula Ic are selected from the compounds preferred in Preferred 8a through 12a.

As noted above, each J is independently a phenyl ring or a 5- or 6-membered heteroaromatic ring wherein each ring is substituted with 1 to 4 R⁵. An example of phenyl substituted with 1 to 4 R⁵ is the ring illustrated as U-1 in Exhibit 1, wherein R^(v) is R⁵ and r is an integer from 1 to 4. Examples of 5- or 6-membered heteroaromatic rings optionally substituted with 1 to 4 R⁵ include the rings U-2 through U-53 illustrated in Exhibit 1 wherein R^(v) is R⁵ and r is an integer from 1 to 4. Note that J-1 through J-4 above also denote 5- or 6-membered heteroaromatic rings. Note that U-2 through U-20 are examples of J-1, U-21 through U-35 and U40 are examples of J-2, U-41 through U-48 are examples of J-3 and U-49 through U-53 are examples of J-4.

Note that when R^(v) is H when attached to an atom, this is the same as if said atom is unsubstituted. The nitrogen atoms that require substitution to fill their valence are substituted with H or R^(v). Note that some U groups can only be substituted with less than 4 R^(v) groups (e.g. U-14, U-15, U-18 through U-21 and U-32 through U-34 can only be substituted with one R^(v)). Note that when the attachment point between (R^(v))_(r) and the U group is illustrated as floating, (R^(v))_(r) can be attached to any available carbon atom of the U group.

The compounds of Formula I and Formula II can be prepared by one or more of the following methods and variations as described in Schemes 1-11. The definitions of R¹, R², R³, R⁴, A, B, M, M¹ and n in the compounds described in the Schemes below are as defined above in the Summary of the Invention or their subsets unless otherwise indicated. Compounds of Formulae Ia-d are subsets of the compounds of Formula I.

As illustrated in Scheme 1, compounds of Formula I can be prepared by coupling compounds of Formula 1 with either iso(thio)cyanates of Formula 2a or (thio)carbamyl chlorides of Formula 2b. In the case of the (thio)carbamyl chloride reaction the presence of an acid acceptor is advantageous. Tertiary amines and alkali (such as lithium, sodium or potassium) carbonates and acetates are preferred as acid acceptors. Triethylamine is especially preferred. The reaction can be carried out at temperatures in the range of −30 to 120° C. The reaction can be carried out in a variety of aprotic solvents which do not react with iso(thio)cyanates and (thio)carbamyl chlorides. Preferred solvents include, for example but not limited to, dichloromethane, toluene, ether, ethyl acetate and chloroform. General synthetic methods to prepare iso(thio)cyanates and (thio)carbamyl chlorides from their amine precursors can be found in WO 01/56962, EP 1006102 and EP 919542. The said amine precursors can be prepared by methods disclosed in WO 02/32856.

Compounds of Formula 1 can be synthesized by removal of the BOC (i.e. t-BuOOC) group found in compounds of Formula 3 as shown in Scheme 2. Reaction of a compound of Formula 3 with an acid in the presence of a suitable solvent produces a compound of Formula 1. A wide variety of acids can be used for the deprotection, including, for example but not limited to, hydrochloric acid, hydrobromic acid, triflic acid, trifluoracetic acid, acetic acid, and methanesulfonic acid. Suitable solvents include both aqueous and organic solvents. A preferred combination of acid and solvent is trifluoroacetic acid in dichloromethane.

Compounds of Formula 3 can be prepared by lithiation of compounds of Formula 4 followed by quenching with either iso(thio)cyanates of Formula 5a or (thio)carbamyl chlorides of Formula 5b as shown in Scheme 3 (using iso(thio)cyanates of Formula 5a, R³ in the product of Formula 3 is H). The lithiation can be carried out with an alkyl lithium reagent or a lithium dialkylamide reagent at temperatures in the range of −100 to 0° C. The preferred conditions involve the use of t-butyllithium in ether at −78° C. After addition of iso(thio)cyanates or (thio)carbamyl chlorides the reaction is allowed to warm to room temperature or is heated to temperatures between 20 and 120° C. For a leading reference to the lithiation of indolines (M and M¹ are independently CR⁶R⁷ and the bond between M and M¹ is a single bond) see, Iwao and Kuraishi, Heterocycles, 1992, 34, 1031-1038. Iso(thio)cyanates of Formula 5a and (thio)carbamyl chlorides of Formula 5b are commercially available, well known in the chemical literature or can be made by general methods known in the chemical literature.

As shown in Scheme 4, a compound of Formula 4 can be prepared by reaction of a heterocycle of Formula 6 with di-tert-butyl dicarbonate. The reaction can be carried out at temperatures in the range of −70 to 120° C. in the presence of an acid acceptor. Tertiary amines and alkali (such as lithium, sodium or potassium) carbonates, hydroxides and acetates are preferred as acid acceptors. Triethylamine is especially preferred. The reaction is generally conducted in a solvent, such as dichloromethane, toluene, ether, ethyl acetate and chloroform.

Compounds of Formula II can be prepared by reaction of compounds of Formula 7 with either iso(thio)cyanates of Formula 5a or (thio)carbamyl chlorides of Formula 5b as shown in Scheme 5. In the case of the (thio)carbamyl chloride reaction, the presence of an acid acceptor is advantageous. Tertiary amines and alkali (such as lithium, sodium or potassium) carbonates and acetates are preferred as acid acceptors. Triethylamine is especially preferred. The reaction can be carried out at temperatures in the range of −30 to 120° C. The reaction can be carried out in a variety of aprotic solvents which do not react with iso(thio)cyanates and (thio)carbamyl chlorides. Preferred solvents include, for example, dichloromethane, toluene, ether, ethyl acetate and chloroform.

Compounds of Formula 7 can be prepared by removal the BOC (i.e. t-BuOOC) group found in compounds of Formula 8 as shown in Scheme 6. The reaction conditions for this deprotection are already described for the conversion of the compounds of Formula 3 to the compounds of Formula 1 in Scheme 2.

Compounds of Formula 8 can be prepared by lithiation of compounds of Formula 4 followed by quenching with either iso(thio)cyanates of Formula 2a or (thio)carbamyl chlorides of Formula 2b as shown in Scheme 7. The reaction conditions for this conversion are already described for the conversion of the compounds of Formula 4 to the compounds of Formula 3 in Scheme 3.

As shown in Scheme 8, alkylation of a compound of Formula 3a with an alkylating agent of Formula 9 in the presence of a base will provide a compound of Formula 3b wherein R³ is other than H. Compounds of Formula 3a are a subset of compounds of Formula 3 wherein R³ is H. Compounds of Formula 3b are also a subset of compounds of Formula 3 wherein R³ is other than H. In the alkylating agent of Formula 9, X is a leaving group such as halogen (e.g., Br, I), OS(O)₂CH₃ (methanesulfonate), OS(O)₂CF₃, OS(O)₂Ph-p-CH₃ (p-toluenesulfonate), and the like. Examples of suitable bases include alkali (such as lithium, sodium or potassium) metal hydroxides, carbonates, hydrides and alkoxides. The reaction is generally conducted in a suitable solvent such as tetrahydrofuran, dioxane, dimethylsulfoxide and N,N-dimethylacetamide. Other examples of suitable solvents, particularly useful when alkali alkoxides are used as bases, include alcohols such as methanol and ethanol. Preferred conditions involve the use of sodium hydride as a base and N,N-dimethylformamide as a solvent.

As an alternative method to that illustrated in Scheme 2, compounds of Formula 1 can also be prepared by amide formation of compounds of Formula 10 in the presence of an organic dehydrating reagent outlined in Scheme 9. This involves direct dehydrative coupling of a carboxylic acid of Formula 10 with an amine of Formula 11. The dehydrating reagent can be, for example, 1,3-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC), carbonyl diimidazole, 2-chloro-N-methylpyridinium iodide (Mukaiyama's reagent), benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP chloride). Various polymer-bound versions of these reagents (e.g., polystyrene-supported DCC) can be used. The amide formation is generally conducted in the presence of a base such as triethylamine and diisopropylethylamine. The preferred conditions involve the use of BOP chloride as a dehydrating reagent and triethylamine as a base in acetonitrile at temperatures in the range of 0 to 120° C. This reaction is well known in the art, and a multitude of conditions and methods can be utilized. Benzotriazole carboxylic acids (compounds of Formula 10 wherein M and M¹ are both N and the bond between them is an aromatic bond) are known in the art (see Japanese Kokai 11171872; Can. J. Chem. 1977, 55, 1653-1657; and Arch. Pharm. (Weinheim, Ger.), 1989, 322, 457-459). Benzimidazole carboxylic acids (compounds of Formula 10 wherein M is N and M¹ is CR⁶ and the bond between them is an aromatic bond) are also known in the art (see Can. J. Chem. 1977, 55, 1653-1657; J. Med. Chem. 1992, 35, 4595-601; Bioorg. Med. Chem. Lett. 1996, 6, 1195-1198; and J. Med. Chem. 1999, 42, 5020-5028). Indazole carboxylic acids (compounds of Formula 10 wherein M is CR⁶ and M¹ is N and the bond between them is an aromatic bond) are also known in the art (see J. Org. Chem. 1980, 45, 3072-7; and Heterocycles 1997, 45, 1833-1838). Indole carboxylic acids (compounds of Formula 10 wherein M and M¹ are independently CR⁶ and the bond between them is an aromatic bond) are also known in the art (see J. Med. Chem. 1996, 39, 4692-4703).

The carboxylic acids of Formula 10a can be prepared by the hydrolysis of thioesters of Formula 12 as shown in Scheme 10. Compounds of Formula 10a is a subset of compounds of Formula 10 where in M and M¹ are independently CR⁶R⁷ and the bond between them is a single bond. This hydrolysis can be carried out in C₁-C₄ alcohols (such as methanol and ethanol) with alkali (such as lithium, sodium and potassium) metal hydroxides. The preferred reaction conditions include the use of potassium or sodium hydroxide as a base and methanol or ethanol as a solvent at temperatures in the range of 20 to 120° C. Compounds of Formula 12 are known in the art and can be prepared by the Sugasawa reaction (Sugasawa et. al. Synthetic Communications, 1990, 20, 71-84).

Indolines of Formula Ia can be oxidized to indoles of Formula Ib as depicted in Scheme 11. Oxidation can be accomplished by using reagents such as 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), chloranil or manganese dioxide. Oxidations of indolines to indoles are generally well known in the art. For leading references see Tetrahedron Lett., 2001, 42(41), 7277-7280; and Tetrahedron Lett., 2000, 41(35), 6721-6724.

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I and Formula II may not be compatible with certain functional groups present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I and II. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I and II.

One skilled in the art will also recognize that compounds of Formula I and II and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without frrther elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. ¹H NMR spectra are reported in ppm downfield from tetramethylsilane: s is singlet, d is doublet, t is triplet, q is quartet, m is multiplet, dd is doublet of doublets, dt is doublet of triplets, br s is broad singlet. m. p. is melting point.

EXAMPLE 1 Preparation of 2,3-dihydro-N⁷-methyl-N¹-[2-methyl-4-(trifluoromethyl)phenyl]-1H-indole-1,7-dicarboxamide

-   Step A: Preparation of 2,3-dihydro-1H-indole-7-carboxylic acid

To a solution of S-methyl 2,3-dihydro-1H-indole-7-carbothioate (Synthetic Communications, 1990, 20, 71-84, 26.88 g) in ethanol (500 mL) was added sodium hydroxide (50% aqueous solution, 50 mL) and the mixture was heated at reflux for 4 hours. Most of the ethanol was removed under reduced pressure. The residue was partitioned between water (150 mL) and dichloromethane (100 mL). The aqueous layer was acidified to pH 3 using concentrated hydrochloric acid, whereupon a solid precipitated. The solid was isolated by filtration and allowed to air dry for 2 hours. The dried solid was dissolved in 300 mL of ethyl acetate and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was evaporated under reduced pressure to give the title compound (13.7 g) as a solid.

¹H NMR (CDCl₃) δ3.08 (2H), 3.75 (2H), 6.59 (1H), 7.20 (1H), 7.61 (1H).

-   Step B: Preparation of 2,3-dihydro-N-methyl-1H-indole-7-carboxamide

To a solution of 2,3-dihydro-1H-indole-7-carboxylic acid (i.e. the product from step A) (1.0 g, 6.1 mmol) in acetonitrile (30 ml) was added sequentially methylamine (Aldrich, 2M in tetrahydrofuran, 6.13 mL), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (i.e. BOP chloride, Aldrich, 1.56 g, 6.1 mmol), and triethylamine (1.71 ml, 12.3 mmol). The reaction mixture was allowed to stir at 25° C. for 48 hours. The mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound.

¹H NMR (CDCl₃) δ2.95 (3H), 3.02 (2H), 3.69 (2H), 6.21 (1 H), 6.31 (1H), 6.61 (1H), 7.1 (2H).

-   Step C: Preparation of     2,3-dihydro-N⁷-methyl-N¹-[2-methyl-4-(trifluoromethyl)phenyl]-1H-indole-1,7-dicarboxamide

To a solution of 2,3-dihydro-N-methyl-1H-indole-7-carboxamide (i.e. the product from Step B) (300 mg) in dichloromethane was added 2-methyl-4-trifluoromethylphenyl isocyanate (0.4 g). After 3 hours the solvent was evaporated under reduced pressure. The residue was triturated with ether, filtered and washed with more ether to provide the title compound (200 mg), a compound of this invention, as a solid melting at 198-200° C.

¹H NMR (CDCl₃) δ2.31 (3H), 2.6 (3H), 3.11 (2H), 4.12 (2H), 6.97 (1H), 7.55 (2H), 8.55 (1H).

EXAMPLE 2 Preparation of 2,3-dihydro-N¹-(1-methylethyl)-N⁷-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1H-indole-1,7-dicarboxamide

-   Step A: Preparation of 1,1-dimethylethyl     2,3-dihydro-7-[[[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]1H-indole-1-carboxylate

To a stirring solution of 1,1-dimethylethyl 2,3-dihydro-1H-indole-1-carboxylate (Aldrich, 1.0 g, 4.5 mmol), N,N,N′N′-tetramethylethylenediamine (0.90 mL, 690 mg, 6.0 mmol), and anhydrous Et₂O (20 mL) at −78° C., was added sec-butyllithium (4.2 mL, 5.4 mmol, 1.3 M in cyclohexane) dropwise over a 10 min period. The resulting solution was stirred at −78° C. for 1 hour followed by the dropwise addition of 2-methyl-4-heptafluoroisopropylphenyl isocyanate (1.4 g, 4.5 mmol) over a 4 min period. The solution was allowed to warm to room temperature over 1 hour followed by the addition of saturated aqueous NH₄Cl (4 mL). The mixture was partitioned between Et₂O and H₂O. The combined organic extract was dried (MgSO₄) and concentrated in vacuo. The residue was subjected to chromatography on silica gel with 30% EtOAc/hexanes as eluent to give the title compound of Step A (1.6 g, 3.1 mmol, 69% yield) as a white solid:

¹H NMR (CDCl₃) δ1.29 (s, 9H), 2.32 (s, 3H), 3.12 (t, 2H), 4.18 (t, 2H), 7.16 (t, 1H), 7.31-7.39 (m, 2H), 7.43 (d, 1H), 7.61 (d, 1H), 7.81 (bs, 1H), 8.59 (d, 1H).

-   Step B: Preparation of     2.3-dihydro-N-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1H-indole-7-carboxamide

A solution of 1,1-dimethylethyl 2,3-dihydro-7-[[[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-1H-indole-1-carboxylate (i.e. the product from Step A) (1.1 g, 2.1 mmol), trifluoroacetic acid (15 mL), and CH₂Cl₂ (50 ml) was stirred at room temperature for 2 hours. The solution was carefully poured into a saturated aqueous solution of NaHCO₃ (500 mL). The mixture was partitioned between CH₂Cl₂ and H₂O. The combined organic extract was dried (MgSO₄) and concentrated in vacuo. The residue was subjected to chromatography on silica gel with 30% EtOAc/hexanes as eluent to give the title compound (800 mg, 1.9 mmol, 90% yield) as a white solid

¹H NMR (CDCl₃) δ2.40 (s, 3H), 3.08 (t, 2H), 3.73 (t, 2H), 6.37 (bs, 1H), 6.63(t, 1H), 7.18-7.28 (m, 3H), 7.47 (d, 1H), 7.80 (s, 1H), 8.22(d, 1H).

-   Step C: Preparation of     2,3-dihydro-N¹-(1-methylethyl)-N⁷-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1-1H-indole-1,7-dicarboxamide

A solution of the product of Step B (200 mg, 0.48 mmol), isopropyl isocyanate (0.10 mL, 87 mg, 1.00 mmol), and CH₂Cl₂ (10 ml) was stirred at room temperature for 17 hours. The mixture was filtered and the residue was washed with a 1/1 solution of Et₂O/CH₂Cl₂ (3 mL) to give the title compound (1.6 g, 3.1 mmol, 69% yield), a compound of this invention, as a white solid.

¹H NMR (DMSO-d₆) δ0.98 (d, 6H), 2.37 (s, 3H), 3.21 (t, 2H), 3.62-3.71 (m, 1H), 4.01 (t, 1H), 6.73 (d, 1H), 7.00 (t, 1H), 7.32(d, 2H), 7.41-7.45 (m, 2H), 8.14 (d, 1H), 9.24 (s, 1H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 14 can be prepared. The following abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, i is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, t-Bu is tert butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, NO₂ is nitro, TMS is trimethylsilyl, S(O)Me is methylsulfinyl, and S(O)₂Me is methylsulfonyl. TABLE 1

R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H Me H OCF₃ Me H Me H OCHF₂ Me H Me H C₂F₅ Me H Me H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H Me H i-C₃F₇ Me H Me H Br Me H Me H Cl Me H Me H SCF₃ Me H Me Me CF₃ Me H Me Me OCF₃ Me H Me Me OCHF₂ Me H Me Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H Me Me Br Me H Me Me Cl Me H Me Me SCF₃ Me H Me Me I Me H Me Me SMe Me H Me Me OMe Me H Me Me OEt Me H Me Me Et Me H Me Me SO₂Me Me H Me Me SO₂CF₃ Me H Me Et CF₃ Me H Me Et Br Me H Me Et Cl Me H Me Ph CF₃ Me H Me Ph Br Me H Me Ph Cl Me H Me 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H Me 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H Me F CF₃ Me H Me Cl CF₃ Me H Me n-Pr CF₃ Me H Me i-Pr CF₃ Me H Me CF₃ CF₃ Me H Me OMe CF₃ Me H Me 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2-py- CF₃ ridyl Me H Me 3-Me-2-pyridyl CF₃ Et H Me H CF₃ Et H Me H C₂F₅ Et H Me H OCF₃ Et H Me Me CF₃ Et H Me Me C₂F₅ Et H Me Me OCF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₂ Me Me H H C₂F₅ Me Me H H OCF₂CHF₂ Me Me H H SCF₂CHF₂ Me Me H H n-C₃F₇ Me Me H H i-C₃F₇ Me Me H H Br Me Me H H Cl Me Me H H SCF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₂ Me Me H Me C₂F₅ Me Me H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ Me Me H Me i-C₃F₇ Me Me H Me Br Me Me H Me Cl Me Me H Me SCF₃ Me Me H Me I Me Me H Me SMe Me Me H Me OMe Me Me H Me OEt Me Me H Me Et Me Me H Me SO₂Me Me Me H Me SO₂CF₃ Me Me H Et CF₃ Me Me H Et Br Me Me H Et Cl Me Me H Ph CF₃ Me Me H Ph Br Me Me H Ph Cl Me Me H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl Me Me H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ Me Me H 2-ClPh Br Me Me H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl Me Me H CF₃ Me Me Me H F CF₃ Me Me H Cl CF₃ Me Me H n-Pr CF₃ Me Me H i-Pr CF₃ Me Me H CF₃ CF₃ Me Me H OMe CF₃ Me Me H 2-BrPh CF₃ Me Me H 2-MePh CF₃ Me Me H 2-CNPh CF₃ Me Me H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2-py- CF₃ ridyl Me Me H 3-Me-2-pyridyl CF₃ Et Me H H CF₃ Et Me H H C₂F₅ Et Me H H OCF₃ Et Me H Me CF₃ Et Me H Me C₂F₅ Et Me H Me OCF₃ Me Cl H H CF₃ Me Cl H H OCF₃ Me Cl H H OCHF₂ Me Cl H H C₂F₅ Me Cl H H OCF₂CHF₂ Me Cl H H SCF₂CHF₂ Me Cl H H n-C₃F₇ Me Cl H H i-C₃F₇ Me Cl H H Br Me Cl H H Cl Me Cl H H SCF₃ Me Cl H Me CF₃ Me Cl H Me OCF₃ Me Cl H Me OCHF₂ Me Cl H Me C₂F₅ Me Cl H Me OCF₂CHF₂ Me Cl H Me SCF₂CHF₂ Me Cl H Me n-C₃F₇ Me Cl H Me i-C₃F₇ Me Cl H Me Br Me Cl H Me Cl Me Cl H Me SCF₃ Me Cl H Me I Me Cl H Me SMe Me Cl H Me OMe Me Cl H Me OEt Me Cl H Me Et Me Cl H Me SO₂Me Me Cl H Me SO₂CF₃ Me Cl H Et CF₃ Me Cl H Et Br Me Cl H Et Cl Me Cl H Ph CF₃ Me Cl H Ph Br Me Cl H Ph Cl Me Cl H 2-pyridyl CF₃ Me Cl H 2-pyridyl Cl CH(Me)CH₂SMe H Me H CF₃ CH(Me)CH₂SMe H Me H OCF₃ CH(Me)CH₂SMe H Me H OCHF₂ CH(Me)CH₂SMe H Me H C₂F₅ CH(Me)CH₂SMe H Me H OCF₂CHF₂ CH(Me)CH₂SMe H Me H SCF₂CHF₂ CH(Me)CH₂SMe H Me H n-C₃F₇ CH(Me)CH₂SMe H Me H i-C₃F₇ CH(Me)CH₂SMe H Me H Br CH(Me)CH₂SMe H Me H Cl CH(Me)CH₂SMe H Me H SCF₃ CH(Me)CH₂SMe H Me Me CF₃ CH(Me)CH₂SMe H Me Me OCF₃ CH(Me)CH₂SMe H Me Me OCHF₂ CH(Me)CH₂SMe H Me Me C₂F₅ CH(Me)CH₂SMe H Me Me OCF₂CHF₂ CH(Me)CH₂SMe H Me Me SCF₂CHF₂ CH(Me)CH₂SMe H Me Me n-C₃F₇ CH(Me)CH₂SMe H Me Me i-C₃F₇ CH(Me)CH₂SMe H Me Me Br CH(Me)CH₂SMe H Me Me Cl CH(Me)CH₂SMe H Me Me SCF₃ CH(Me)CH₂SMe H Me Me I CH(Me)CH₂SMe H Me Me SMe CH(Me)CH₂SMe H Me Me OMe CH(Me)CH₂SMe H Me Me OEt CH(Me)CH₂SMe H Me Me Et CH(Me)CH₂SMe H Me Me SO₂Me CH(Me)CH₂SMe H Me Me SO₂CF₃ CH(Me)CH₂SMe H Me Et CF₃ CH(Me)CH₂SMe H Me Et Br CH(Me)CH₂SMe H Me Et Cl CH(Me)CH₂SMe H Me Ph CF₃ CH(Me)CH₂SMe H Me Ph Br CH(Me)CH₂SMe H Me Ph Cl CH(Me)CH₂SMe H Me 2-pyridyl CF₃ CH(Me)CH₂SMe H Me 2-pyridyl Cl CH(Me)CH₂SMe H Me 2-ClPh CF₃ CH(Me)CH₂SMe H Me 2-ClPh OCF₃ CH(Me)CH₂SMe H Me 2-ClPh SCHF₂ CH(Me)CH₂SMe H Me 2-ClPh Br CH(Me)CH₂SMe H Me 2-ClPh Cl CH(Me)CH₂SMe H Me 3-Cl-2-pyridyl CF₃ CH(Me)CH₂SMe H Me 3-Cl-2-pyridyl OCF₃ CH(Me)CH₂SMe H Me 3-Cl-2-pyridyl SCHF₂ CH(Me)CH₂SMe H Me 3-Cl-2-pyridyl Br CH(Me)CH₂SMe H Me 3-Cl-2-pyridyl Cl CH(Me)CH₂SMe H Me 3-Br-2-pyridyl CF₃ CH(Me)CH₂SMe H Me 3-Br-2-pyridyl OCF₃ CH(Me)CH₂SMe H Me 3-Br-2-pyridyl Br CH(Me)CH₂SMe H Me 3-Br-2-pyridyl Cl CH(Me)CH₂SMe H Me CF₃ Me CH(Me)CH₂SMe H Me F CF₃ CH(Me)CH₂SMe H Me Cl CF₃ CH(Me)CH₂SMe H Me n-Pr CF₃ CH(Me)CH₂SMe H Me i-Pr CF₃ CH(Me)CH₂SMe H Me CF₃ CF₃ CH(Me)CH₂SMe H Me OMe CF₃ CH(Me)CH₂SMe H Me 2-BrPh CF₃ CH(Me)CH₂SMe H Me 2-MePh CF₃ CH(Me)CH₂SMe H Me 2-CNPh CF₃ CH(Me)CH₂SMe H Me 2-FPh CF₃ CH(Me)CH₂SMe H Me 2,6-F₂Ph CF₃ CH(Me)CH₂SMe H Me 2,4-F₂Ph CF₃ CH(Me)CH₂SMe H Me 2,5-F₂Ph CF₃ CH(Me)CH₂SMe H Me 2-MeOPh CF₃ CH(Me)CH₂SMe H Me 3-F-2-pyridyl CF₃ CH(Me)CH₂SMe H Me 3-CF₃-2-py- CF₃ ridyl CH(Me)CH₂SMe H Me 3-Me-2-pyridyl CF₃ CH(Me)CH₂SMe Me H H CF₃ CH(Me)CH₂SMe Me H H OCF₃ CH(Me)CH₂SMe Me H H OCHF₂ CH(Me)CH₂SMe Me H H C₂F₅ CH(Me)CH₂SMe Me H H OCF₂CHF₂ CH(Me)CH₂SMe Me H H SCF₂CHF₂ CH(Me)CH₂SMe Me H H n-C₃F₇ CH(Me)CH₂SMe Me H H i-C₃F₇ CH(Me)CH₂SMe Me H H Br CH(Me)CH₂SMe Me H H Cl CH(Me)CH₂SMe Me H H SCF₃ CH(Me)CH₂SMe Me H H CF₃ CH(Me)CH₂SMe Me H H OCF₃ CH(Me)CH₂SMe Me H H OCHF₂ CH(Me)CH₂SMe Me H Me C₂F₅ CH(Me)CH₂SMe Me H Me OCF₂CHF₂ CH(Me)CH₂SMe Me H Me SCF₂CHF₂ CH(Me)CH₂SMe Me H Me n-C₃F₇ CH(Me)CH₂SMe Me H Me i-C₃F₇ CH(Me)CH₂SMe Me H Me Br CH(Me)CH₂SMe Me H Me Cl CH(Me)CH₂SMe Me H Me SCF₃ CH(Me)CH₂SMe Me H Me I CH(Me)CH₂SMe Me H Me SMe CH(Me)CH₂SMe Me H Me OMe CH(Me)CH₂SMe Me H Me OEt CH(Me)CH₂SMe Me H Me Et CH(Me)CH₂SMe Me H Me SO₂Me CH(Me)CH₂SMe Me H Me SO₂CF₃ CH(Me)CH₂SMe Me H Et CF₃ CH(Me)CH₂SMe Me H Et Br CH(Me)CH₂SMe Me H Et Cl CH(Me)CH₂SMe Me H Ph CF₃ CH(Me)CH₂SMe Me H Ph Br CH(Me)CH₂SMe Me H Ph Cl CH(Me)CH₂SMe Me H 2-pyridyl CF₃ CH(Me)CH₂SMe Me H 2-pyridyl Cl CH(Me)CH₂SMe Me H 2-ClPh CF₃ CH(Me)CH₂SMe Me H 2-ClPh OCF₃ CH(Me)CH₂SMe Me H 2-ClPh SCHF₂ CH(Me)CH₂SMe Me H 2-ClPh Br CH(Me)CH₂SMe Me H 2-ClPh Cl CH(Me)CH₂SMe Me H 3-Cl-2-pyridyl CF₃ CH(Me)CH₂SMe Me H 3-Cl-2-pyridyl OCF₃ CH(Me)CH₂SMe Me H 3-Cl-2-pyridyl SCHF₂ CH(Me)CH₂SMe Me H 3-Cl-2-pyridyl Br CH(Me)CH₂SMe Me H 3-Cl-2-pyridyl Cl CH(Me)CH₂SMe Me H 3-Br-2-pyridyl CF₃ CH(Me)CH₂SMe Me H 3-Br-2-pyridyl OCF₃ CH(Me)CH₂SMe Me H 3-Br-2-pyridyl Br CH(Me)CH₂SMe Me H 3-Br-2-pyridyl Cl CH(Me)CH₂SMe Me H CF₃ Me CH(Me)CH₂SMe Me H F CF₃ CH(Me)CH₂SMe Me H Cl CF₃ CH(Me)CH₂SMe Me H n-Pr CF₃ CH(Me)CH₂SMe Me H i-Pr CF₃ CH(Me)CH₂SMe Me H CF₃ CF₃ CH(Me)CH₂SMe Me H OMe CF₃ CH(Me)CH₂SMe Me H 2-BrPh CF₃ CH(Me)CH₂SMe Me H 2-MePh CF₃ CH(Me)CH₂SMe Me H 2-CNPh CF₃ CH(Me)CH₂SMe Me H 2-FPh CF₃ CH(Me)CH₂SMe Me H 2,6-F₂Ph CF₃ CH(Me)CH₂SMe Me H 2,4-F₂Ph CF₃ CH(Me)CH₂SMe Me H 2,5-F₂Ph CF₃ CH(Me)CH₂SMe Me H 2-MeOPh CF₃ CH(Me)CH₂SMe Me H 3-F-2-pyridyl CF₃ CH(Me)CH₂SMe Me H 3-CF₃-2-py- CF₃ ridyl CH(Me)CH₂SMe Me H 3-Me-2-pyridyl CF₃ Me H H H CF₃ Me H H H OCF₃ Me H H H OCHF₂ Me H H H C₂F₅ Me H H H OCF₂CHF₂ Me H H H SCF₂CHF₂ Me H H H n-C₃F₇ Me H H H i-C₃F₇ Me H H H Br Me H H H Cl Me H H H SCF₃ Me H H Me CF₃ Me H H Me OCF₃ Me H H Me OCHF₂ Me H H Me C₂F₅ Me H H Me OCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H H Me n-C₃F₇ Me H H Me i-C₃F₇ Me H H Me Br Me H H Me Cl Me H H Me SCF₃ Me H H Me I Me H H Me SMe Me H H Me OMe Me H H Me OEt Me H H Me Et Me H H Me SO₂Me Me H H Me SO₂CF₃ Me H H Et CF₃ Me H H Et Br Me H H Et Cl Me H H Ph CF₃ Me H H Ph Br Me H H Ph Cl Me H H 2-pyridyl CF₃ Me H H 2-pyridyl Cl Me H H 2-ClPh CF₃ Me H H 2-ClPh OCF₃ Me H H 2-ClPh SCHF₂ Me H H 2-ClPh Br Me H H 2-ClPh Cl Me H H 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Cl Me H H 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Cl Me H H CF₃ Me Me H H F CF₃ Me H H Cl CF₃ Me H H n-Pr CF₃ Me H H i-Pr CF₃ Me H H CF₃ CF₃ Me H H OMe CF₃ Me H H 2-BrPh CF₃ Me H H 2-MePh CF₃ Me H H 2-CNPh CF₃ Me H H 2-FPh CF₃ Me H H 2,6-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H H 2-MeOPh CF₃ Me H H 3-F-2-pyridyl CF₃ Me H H 3-CF₃-2-py- CF₃ ridyl Me H H 3-Me-2-pyridyl CF₃ Et H H H CF₃ Et H H H C₂F₅ Et H H H OCF₃ Et H H Me CF₃ Et H H Me C₂F₅ Et H H Me OCF₃ i-Pr H H H CF₃ i-Pr H H H OCF₃ i-Pr H H H OCHF₂ i-Pr H H H C₂F₅ i-Pr H H H OCF₂CHF₂ i-Pr H H H SCF₂CHF₂ i-Pr H H H n-C₃F₇ i-Pr H H H i-C₃F₇ i-Pr H H H Br i-Pr H H H Cl i-Pr H H H SCF₃ i-Pr H H Me CF₃ i-Pr H H Me OCF₃ i-Pr H H Me OCHF₂ i-Pr H H Me C₂F₅ i-Pr H H Me OCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ i-Pr H H Me n-C₃F₇ i-Pr H H Me i-C₃F₇ i-Pr H H Me Br i-Pr H H Me Cl i-Pr H H Me SCF₃ i-Pr H H Me I i-Pr H H Me SMe i-Pr H H Me OMe i-Pr H H Me OEt i-Pr H H Me Et i-Pr H H Me SO₂Me i-Pr H H Me SO₂CF₃ i-Pr H H Et CF₃ i-Pr H H Et Br i-Pr H H Et Cl i-Pr H H Ph CF₃ i-Pr H H Ph Br i-Pr H H Ph Cl i-Pr H H 2-pyridyl CF₃ i-Pr H H 2-pyridyl Cl i-Pr H H 2-ClPh CF₃ i-Pr H H 2-ClPh OCF₃ i-Pr H H 2-ClPh SCHF₂ i-Pr H H 2-ClPh Br i-Pr H H 2-ClPh Cl i-Pr H H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-Cl-2-pyridyl Br i-Pr H H 3-Cl-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Cl i-Pr H H CF₃ Me i-Pr H H F CF₃ i-Pr H H Cl CF₃ i-Pr H H n-Pr CF₃ i-Pr H H i-Pr CF₃ i-Pr H H CF₃ CF₃ i-Pr H H OMe CF₃ i-Pr H H 2-BrPh CF₃ i-Pr H H 2-MePh CF₃ i-Pr H H 2-CNPh CF₃ i-Pr H H 2-FPh CF₃ i-Pr H H 2,6-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ i-Pr H H 2-MeOPh CF₃ i-Pr H H 3-F-2-pyridyl CF₃ i-Pr H H 3-CF₃-2-py- CF₃ ridyl i-Pr H H 3-Me-2-pyridyl CF₃ i-Pr Me H H CF₃ i-Pr Me H H C₂F₅ i-Pr Me H H OCF₃ i-Pr Me H Me CF₃ i-Pr Me H Me C₂F₅ i-Pr Me H Me OCF₃ Me Cl H 2-ClPh CF₃ Me Cl H 2-ClPh OCF₃ Me Cl H 2-ClPh SCHF₂ Me Cl H 2-ClPh Br Me Cl H 2-ClPh Cl Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H 3-Cl-2-pyridyl Br Me Cl H 3-Cl-2-pyridyl Cl Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H 3-Br-2-pyridyl Cl Me Cl H CF₃ Me Me Cl H F CF₃ Me Cl H Cl CF₃ Me Cl H n-Pr CF₃ Me Cl H i-Pr CF₃ Me Cl H CF₃ CF₃ Me Cl H OMe CF₃ Me Cl H 2-BrPh CF₃ Me Cl H 2-MePh CF₃ Me Cl H 2-CNPh CF₃ Me Cl H 2-FPh CF₃ Me Cl H 2,6-F₂Ph CF₃ Me Cl H 2,4-F₂Ph CF₃ Me Cl H 2,5-F₂Ph CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H 3-CF₃-2-py- CF₃ ridyl Me Cl H 3-Me-2-pyridyl CF₃ Et Cl H H OCF₃ Et Cl H H C₂F₅ Et Cl H Me CF₃ Et Cl H Me C₂F₅ i-Pr Cl H Me CF₃ CH(Me)CH₂SMe H H H CF₃ CH(Me)CH₂SMe H H H OCF₃ CH(Me)CH₂SMe H H H OCHF₂ CH(Me)CH₂SMe H H H C₂F₅ CH(Me)CH₂SMe H H H OCF₂CHF₂ CH(Me)CH₂SMe H H H SCF₂CHF₂ CH(Me)CH₂SMe H H H n-C₃F₇ CH(Me)CH₂SMe H H H i-C₃F₇ CH(Me)CH₂SMe H H H Br CH(Me)CH₂SMe H H H Cl CH(Me)CH₂SMe H H H SCF₃ CH(Me)CH₂SMe H H Me CF₃ CH(Me)CH₂SMe H H Me OCF₃ CH(Me)CH₂SMe H H Me OCHF₂ CH(Me)CH₂SMe H H Me C₂F₅ CH(Me)CH₂SMe H H Me OCF₂CHF₂ CH(Me)CH₂SMe H H Me SCF₂CHF₂ CH(Me)CH₂SMe H H Me n-C₃F₇ CH(Me)CH₂SMe H H Me i-C₃F₇ CH(Me)CH₂SMe H H Me Br CH(Me)CH₂SMe H H Me Cl CH(Me)CH₂SMe H H Me SCF₃ CH(Me)CH₂SMe H H Me I CH(Me)CH₂SMe H H Me SMe CH(Me)CH₂SMe H H Me OMe CH(Me)CH₂SMe H H Me OEt CH(Me)CH₂SMe H H Me Et CH(Me)CH₂SMe H H Me SO₂Me CH(Me)CH₂SMe H H Me SO₂CF₃ CH(Me)CH₂SMe H H Et CF₃ CH(Me)CH₂SMe H H Et Br CH(Me)CH₂SMe H H Et Cl CH(Me)CH₂SMe H H Ph CF₃ CH(Me)CH₂SMe H H Ph Br CH(Me)CH₂SMe H H Ph Cl CH(Me)CH₂SMe H H 2-pyridyl CF₃ CH(Me)CH₂SMe H H 2-pyridyl Cl CH(Me)CH₂SMe H H 2-ClPh CF₃ CH(Me)CH₂SMe H H 2-ClPh OCF₃ CH(Me)CH₂SMe H H 2-ClPh SCHF₂ CH(Me)CH₂SMe H H 2-ClPh Br CH(Me)CH₂SMe H H 2-ClPh Cl CH(Me)CH₂SMe H H 3-Cl-2-pyridyl CF₃ CH(Me)CH₂SMe H H 3-Cl-2-pyridyl OCF₃ CH(Me)CH₂SMe H H 3-Cl-2-pyridyl SCHF₂ CH(Me)CH₂SMe H H 3-Cl-2-pyridyl Br CH(Me)CH₂SMe H H 3-Cl-2-pyridyl Cl CH(Me)CH₂SMe H H 3-Br-2-pyridyl CF₃ CH(Me)CH₂SMe H H 3-Br-2-pyridyl OCF₃ CH(Me)CH₂SMe H H 3-Br-2-pyridyl Br CH(Me)CH₂SMe H H 3-Br-2-pyridyl Cl CH(Me)CH₂SMe H H CF₃ Me CH(Me)CH₂SMe H H F CF₃ CH(Me)CH₂SMe H H Cl CF₃ CH(Me)CH₂SMe H H n-Pr CF₃ CH(Me)CH₂SMe H H i-Pr CF₃ CH(Me)CH₂SMe H H CF₃ CF₃ CH(Me)CH₂SMe H H OMe CF₃ CH(Me)CH₂SMe H H 2-BrPh CF₃ CH(Me)CH₂SMe H H 2-MePh CF₃ CH(Me)CH₂SMe H H 2-CNPh CF₃ CH(Me)CH₂SMe H H 2-FPh CF₃ CH(Me)CH₂SMe H H 2,6-F₂Ph CF₃ CH(Me)CH₂SMe H H 2,4-F₂Ph CF₃ CH(Me)CH₂SMe H H 2,5-F₂Ph CF₃ CH(Me)CH₂SMe H H 2-MeOPh CF₃ CH(Me)CH₂SMe H H 3-F-2-pyridyl CF₃ CH(Me)CH₂SMe H H 3-CF₃-2-py- CF₃ ridyl CH(Me)CH₂SMe H H 3-Me-2-pyridyl CF₃ CH(Me)CH₂SMe Cl H 2-ClPh CF₃ CH(Me)CH₂SMe Cl H 2-ClPh OCF₃ CH(Me)CH₂SMe Cl H 2-ClPh SCHF₂ CH(Me)CH₂SMe Cl H 2-ClPh Br CH(Me)CH₂SMe Cl H 2-ClPh Cl CH(Me)CH₂SMe Cl H 3-Cl-2-pyridyl CF₃ CH(Me)CH₂SMe Cl H 3-Cl-2-pyridyl OCF₃ CH(Me)CH₂SMe Cl H 3-Cl-2-pyridyl SCHF₂ CH(Me)CH₂SMe Cl H 3-Cl-2-pyridyl Br CH(Me)CH₂SMe Cl H 3-Cl-2-pyridyl Cl CH(Me)CH₂SMe Cl H 3-Br-2-pyridyl CF₃ CH(Me)CH₂SMe Cl H 3-Br-2-pyridyl OCF₃ CH(Me)CH₂SMe Cl H 3-Br-2-pyridyl Br CH(Me)CH₂SMe Cl H 3-Br-2-pyridyl Cl CH(Me)CH₂SMe Cl H CF₃ Me CH(Me)CH₂SMe Cl H F CF₃ CH(Me)CH₂SMe Cl H Cl CF₃ CH(Me)CH₂SMe Cl H n-Pr CF₃ CH(Me)CH₂SMe Cl H i-Pr CF₃ CH(Me)CH₂SMe Cl H CF₃ CF₃ CH(Me)CH₂SMe Cl H OMe CF₃ CH(Me)CH₂SMe Cl H 2-BrPh CF₃ CH(Me)CH₂SMe Cl H 2-MePh CF₃ CH(Me)CH₂SMe Cl H 2-CNPh CF₃ CH(Me)CH₂SMe Cl H 2-FPh CF₃ CH(Me)CH₂SMe Cl H 2,6-F₂Ph CF₃ CH(Me)CH₂SMe Cl H 2,4-F₂Ph CF₃ CH(Me)CH₂SMe Cl H 2,5-F₂Ph CF₃ CH(Me)CH₂SMe Cl H 2-MeOPh CF₃ CH(Me)CH₂SMe Cl H 3-F-2-pyridyl CF₃ CH(Me)CH₂SMe Cl H 3-CF₃-2-py- CF₃ ridyl CH(Me)CH₂SMe Cl H 3-Me-2-pyridyl CF₃ CH(Me)CH₂SMe Cl H H CF₃ CH(Me)CH₂SMe Cl H H OCF₃ CH(Me)CH₂SMe Cl H H OCHF₂ CH(Me)CH₂SMe Cl H H C₂F₅ CH(Me)CH₂SMe Cl H H OCF₂CHF₂ CH(Me)CH₂SMe Cl H H SCF₂CHF₂ CH(Me)CH₂SMe Cl H H n-C₃F₇ CH(Me)CH₂SMe Cl H H i-C₃F₇ CH(Me)CH₂SMe Cl H H Br CH(Me)CH₂SMe Cl H H Cl CH(Me)CH₂SMe Cl H H SCF₃ CH(Me)CH₂SMe Cl H Me CF₃ CH(Me)CH₂SMe Cl H Me OCF₃ CH(Me)CH₂SMe Cl H Me OCHF₂ CH(Me)CH₂SMe Cl H Me C₂F₅ CH(Me)CH₂SMe Cl H Me OCF₂CHF₂ CH(Me)CH₂SMe Cl H Me SCF₂CHF₂ CH(Me)CH₂SMe Cl H Me n-C₃F₇ CH(Me)CH₂SMe Cl H Me i-C₃F₇ CH(Me)CH₂SMe Cl H Me Br CH(Me)CH₂SMe Cl H Me Cl CH(Me)CH₂SMe Cl H Me SCF₃ CH(Me)CH₂SMe Cl H Me I CH(Me)CH₂SMe Cl H Me SMe CH(Me)CH₂SMe Cl H Me OMe CH(Me)CH₂SMe Cl H Me OEt CH(Me)CH₂SMe Cl H Me Et CH(Me)CH₂SMe Cl H Me SO₂Me CH(Me)CH₂SMe Cl H Me SO₂CF₃ CH(Me)CH₂SMe Cl H Et CF₃ CH(Me)CH₂SMe Cl H Et Br CH(Me)CH₂SMe Cl H Et Cl CH(Me)CH₂SMe Cl H Ph CF₃ CH(Me)CH₂SMe Cl H Ph Br CH(Me)CH₂SMe Cl H Ph Cl CH(Me)CH₂SMe Cl H 2-pyridyl CF₃ CH(Me)CH₂SMe Cl H 2-pyridyl Cl

TABLE 2

R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H Me H OCF₃ Me H Me H OCHF₂ Me H Me H C₂F₅ Me H Me H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H Me H i-C₃F₇ Me H Me H Br Me H Me H Cl Me H Me H SCF₃ Me H Me Me CF₃ Me H Me Me OCF₃ Me H Me Me OCHF₂ Me H Me Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H Me Me Br Me H Me Me Cl Me H Me Me SCF₃ Me H Me Me I Me H Me Me SMe Me H Me Me OMe Me H Me Me OEt Me H H H CF₃ Me H H H OCF₃ Me H H H OCHF₂ Me H H H C₂F₅ Me H H H OCF₂CHF₂ Me H H H SCF₂CHF₂ Me H H H n-C₃F₇ Me H H H i-C₃F₇ Me H H H Br Me H H H Cl Me H H H SCF₃ Me H H Me CF₃ Me H H Me OCF₃ Me H H Me OCHF₂ Me H H Me C₂F₅ Me H H Me OCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H H Me n-C₃F₇ Me H H Me i-C₃F₇ Me H H Me Br Me H H Me Cl Me H H Me SCF₃ Me H H Me I Me H H Me SMe Me H H Me OMe Me H H Me OEt Me H Me Me Et Me H Me Me SO₂Me Me H Me Me SO₂CF₃ Me H Me Et CF₃ Me H Me Et Br Me H Me Et Cl Me H Me Ph CF₃ Me H Me Ph Br Me H Me Ph Cl Me H Me 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H Me 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H Me F CF₃ Me H Me Cl CF₃ Me H Me n-Pr CF₃ Me H Me i-Pr CF₃ Me H Me CF₃ CF₃ Me H Me OMe CF₃ Me H Me 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H Me Et Me H H Me SO₂Me Me H H Me SO₂CF₃ Me H H Et CF₃ Me H H Et Br Me H H Et Cl Me H H Ph CF₃ Me H H Ph Br Me H H Ph Cl Me H H 2-pyridyl CF₃ Me H H 2-pyridyl Cl Me H H 2-ClPh CF₃ Me H H 2-ClPh OCF₃ Me H H 2-ClPh SCHF₂ Me H H 2-ClPh Br Me H H 2-ClPh Cl Me H H 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Cl Me H H 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Cl Me H H CF₃ Me Me H H F CF₃ Me H H Cl CF₃ Me H H n-Pr CF₃ Me H H i-Pr CF₃ Me H H CF₃ CF₃ Me H H OMe CF₃ Me H H 2-BrPh CF₃ Me H H 2-MePh CF₃ Me H H 2-CNPh CF₃ Me H H 2-FPh CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2-pyridyl CF₃ Me H Me 3-Me-2-pyridyl CF₃ Et H Me H CF₃ Et H Me H C₂F₅ Et H Me H OCF₃ Et H Me Me CF₃ Et H Me Me C₂F₅ Et H Me Me OCF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₂ Me Me H H C₂F₅ Me Me H H OCF₂CHF₂ Me Me H H SCF₂CHF₂ Me Me H H n-C₃F₇ Me Me H H i-C₃F₇ Me Me H H Br Me Me H H Cl Me Me H H SCF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₂ Me Me H Me C₂F₅ Me Me H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ Me Me H Me i-C₃F₇ Me Me H Me Br Me Me H Me Cl Me Me H Me SCF₃ Me Me H Me I Me H H 2,4-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H H 2-MeOPh CF₃ Me H H 3-F-2-pyridyl CF₃ Me H H 3-CF₃-2-pyridyl CF₃ Me H H 3-Me-2-pyridyl CF₃ Et H H H CF₃ Et H H H C₂F₅ Et H H H OCF₃ Et H H Me CF₃ Et H H Me C₂F₅ Et H H Me OCF₃ i-Pr H H H CF₃ i-Pr H H H OCF₃ i-Pr H H H OCHF₂ i-Pr H H H C₂F₅ i-Pr H H H OCF₂CHF₂ i-Pr H H H SCF₂CHF₂ i-Pr H H H n-C₃F₇ i-Pr H H H i-C₃F₇ i-Pr H H H Br i-Pr H H H Cl i-Pr H H H SCF₃ i-Pr H H Me CF₃ i-Pr H H Me OCF₃ i-Pr H H Me OCHF₂ i-Pr H H Me C₂F₅ i-Pr H H Me OCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ i-Pr H H Me n-C₃F₇ i-Pr H H Me i-C₃F₇ i-Pr H H Me Br i-Pr H H Me Cl i-Pr H H Me SCF₃ i-Pr H H Me I Me Me H Me SMe Me Me H Me OMe Me Me H Me OEt Me Me H Me Et Me Me H Me SO₂Me Me Me H Me SO₂CF₃ Me Me H Et CF₃ Me Me H Et Br Me Me H Et Cl Me Me H Ph CF₃ Me Me H Ph Br Me Me H Ph Cl Me Me H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl Me Me H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ Me Me H 2-ClPh Br Me Me H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl Me Me H CF₃ Me Me Me H F CF₃ Me Me H Cl CF₃ Me Me H n-Pr CF₃ Me Me H i-Pr CF₃ Me Me H CF₃ CF₃ Me Me H OMe CF₃ Me Me H 2-BrPh CF₃ Me Me H 2-MePh CF₃ i-Pr H H Me SMe i-Pr H H Me OMe i-Pr H H Me OEt i-Pr H H Me Et i-Pr H H Me SO₂Me i-Pr H H Me SO₂CF₃ i-Pr H H Et CF₃ i-Pr H H Et Br i-Pr H H Et Cl i-Pr H H Ph CF₃ i-Pr H H Ph Br i-Pr H H Ph Cl i-Pr H H 2-pyridyl CF₃ i-Pr H H 2-pyridyl Cl i-Pr H H 2-ClPh CF₃ i-Pr H H 2-ClPh OCF₃ i-Pr H H 2-ClPh SCHF₂ i-Pr H H 2-ClPh Br i-Pr H H 2-ClPh Cl i-Pr H H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-Cl-2-pyridyl Br i-Pr H H 3-Cl-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Cl i-Pr H H CF₃ Me i-Pr H H F CF₃ i-Pr H H Cl CF₃ i-Pr H H n-Pr CF₃ i-Pr H H i-Pr CF₃ i-Pr H H CF₃ CF₃ i-Pr H H OMe CF₃ i-Pr H H 2-BrPh CF₃ i-Pr H H 2-MePh CF₃ Me Me H 2-CNPh CF₃ Me Me H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2-pyridyl CF₃ Me Me H 3-Me-2-pyridyl CF₃ Et Me H H CF₃ Et Me H H C₂F₅ Et Me H H OCF₃ Et Me H Me CF₃ Et Me H Me C₂F₅ Et Me H Me OCF₃ Me Cl H H CF₃ Me Cl H H OCF₃ Me Cl H H OCHF₂ Me Cl H H C₂F₅ Me Cl H H OCF₂CHF₂ Me Cl H H SCF₂CHF₂ Me Cl H H n-C₃F₇ Me Cl H H i-C₃F₇ Me Cl H H Br Me Cl H H Cl Me Cl H H SCF₃ Me Cl H Me CF₃ Me Cl H Me OCF₃ Me Cl H Me OCHF₂ Me Cl H Me C₂F₅ Me Cl H Me OCF₂CHF₂ Me Cl H Me SCF₂CHF₂ Me Cl H Me n-C₃F₇ Me Cl H Me i-C₃F₇ Me Cl H Me Br i-Pr H H 2-CNPh CF₃ i-Pr H H 2-FPh CF₃ i-Pr H H 2,6-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ i-Pr H H 2-MeOPh CF₃ i-Pr H H 3-F-2-pyridyl CF₃ i-Pr H H 3-CF₃-2-pyridyl CF₃ i-Pr H H 3-Me-2-pyridyl CF₃ i-Pr Me H H CF₃ i-Pr Me H H C₂F₅ i-Pr Me H H OCF₃ i-Pr Me H Me CF₃ i-Pr Me H Me C₂F₅ i-Pr Me H Me OCF₃ Me Cl H 2-ClPh CF₃ Me Cl H 2-ClPh OCF₃ Me Cl H 2-ClPh SCHF₂ Me Cl H 2-ClPh Br Me Cl H 2-ClPh Cl Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H 3-Cl-2-pyridyl Br Me Cl H 3-Cl-2-pyridyl Cl Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H 3-Br-2-pyridyl Cl Me Cl H CF₃ Me Me Cl H F CF₃ Me Cl H Cl CF₃ Me Cl H n-Pr CF₃ Me Cl H i-Pr CF₃ Me Cl H CF₃ CF₃ Me Cl H Me Cl Me Cl H Me SCF₃ Me Cl H Me I Me Cl H Me SMe Me Cl H Me OMe Me Cl H Me OEt Me Cl H Me Et Me Cl H Me SO₂Me Me Cl H Me SO₂CF₃ Me Cl H Et CF₃ Me Cl H Et Br Me Cl H Et Cl Me Cl H Ph CF₃ Me Cl H Ph Br Me Cl H Ph Cl Me Cl H 2-pyridyl CF₃ Me Cl H 2-pyridyl Cl Me Cl H OMe CF₃ Me Cl H 2-BrPh CF₃ Me Cl H 2-MePh CF₃ Me Cl H 2-CNPh CF₃ Me Cl H 2-FPh CF₃ Me Cl H 2,6-F₂Ph CF₃ Me Cl H 2,4-F₂Ph CF₃ Me Cl H 2,5-F₂Ph CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H 3-CF₃-2-pyridyl CF₃ Me Cl H 3-Me-2-pyridyl CF₃ Et Cl H H OCF₃ Et Cl H H C₂F₅ Et Cl H Me CF₃ Et Cl H Me C₂F₅ i-Pr Cl H Me CF₃

TABLE 3

R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H Me H OCF₃ Me H Me H OCHF₂ Me H Me H C₂F₅ Me H Me H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H H H CF₃ Me H H H OCF₃ Me H H H OCHF₂ Me H H H C₂F₅ Me H H H OCF₂CHF₂ Me H H H SCF₂CHF₂ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H Me H Br Me H Me H Cl Me H Me H SCF₃ Me H Me Me CF₃ Me H Me Me OCF₃ Me H Me Me OCHF₂ Me H Me Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H Me Me Br Me H Me Me Cl Me H Me Me SCF₃ Me H Me Me I Me H Me Me SMe Me H Me Me OMe Me H Me Me OEt Me H Me Me Et Me H Me Me SO₂Me Me H Me Me SO₂CF₃ Me H Me Et CF₃ Me H Me Et Br Me H Me Et Cl Me H Me Ph CF₃ Me H Me Ph Br Me H Me Ph Cl Me H Me 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H Me 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H H i-C₃F₇ Me H H H Br Me H H H Cl Me H H H SCF₃ Me H H Me CF₃ Me H H Me OCF₃ Me H H Me OCHF₂ Me H H Me C₂F₅ Me H H Me OCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H H Me n-C₃F₇ Me H H Me i-C₃F₇ Me H H Me Br Me H H Me Cl Me H H Me SCF₃ Me H H Me I Me H H Me SMe Me H H Me OMe Me H H Me OEt Me H H Me Et Me H H Me SO₂Me Me H H Me SO₂CF₃ Me H H Et CF₃ Me H H Et Br Me H H Et Cl Me H H Ph CF₃ Me H H Ph Br Me H H Ph Cl Me H H 2-pyridyl CF₃ Me H H 2-pyridyl Cl Me H H 2-ClPh CF₃ Me H H 2-ClPh OCF₃ Me H H 2-ClPh SCHF₂ Me H H 2-ClPh Br Me H H 2-ClPh Cl Me H H 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H Me F CF₃ Me H Me Cl CF₃ Me H Me n-Pr CF₃ Me H Me i-Pr CF₃ Me H Me CF₃ CF₃ Me H Me OMe CF₃ Me H Me 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2-pyridyl CF₃ Me H Me 3-Me-2-pyridyl CF₃ Et H Me H CF₃ Et H Me H C₂F₅ Et H Me H OCF₃ Et H Me Me CF₃ Et H Me Me C₂F₅ Et H Me Me OCF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₂ Me Me H H C₂F₅ Me H H 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Cl Me H H 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Cl Me H H CF₃ Me Me H H F CF₃ Me H H Cl CF₃ Me H H n-Pr CF₃ Me H H i-Pr CF₃ Me H H CF₃ CF₃ Me H H OMe CF₃ Me H H 2-BrPh CF₃ Me H H 2-MePh CF₃ Me H H 2-CNPh CF₃ Me H H 2-FPh CF₃ Me H H 2,6-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H H 2-MeOPh CF₃ Me H H 3-F-2-pyridyl CF₃ Me H H 3-CF₃-2-pyridyl CF₃ Me H H 3-Me-2-pyridyl CF₃ Et H H H CF₃ Et H H H C₂F₅ Et H H H OCF₃ Et H H Me CF₃ Et H H Me C₂F₅ Et H H Me OCF₃ i-Pr H H H CF₃ i-Pr H H H OCF₃ i-Pr H H H OCHF₂ i-Pr H H H C₂F₅ Me Me H H OCF₂CHF₂ Me Me H H SCF₂CHF₂ Me Me H H n-C₃F₇ Me Me H H i-C₃F₇ Me Me H H Br Me Me H H Cl Me Me H H SCF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₂ Me Me H Me C₂F₅ Me Me H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ Me Me H Me i-C₃F₇ Me Me H Me Br Me Me H Me Cl Me Me H Me SCF₃ Me Me H Me I Me Me H Me SMe Me Me H Me OMe Me Me H Me OEt Me Me H Me Et Me Me H Me SO₂Me Me Me H Me SO₂CF₃ Me Me H Et CF₃ Me Me H Et Br Me Me H Et Cl Me Me H Ph CF₃ Me Me H Ph Br Me Me H Ph Cl Me Me H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl Me Me H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ Me Me H 2-ClPh Br i-Pr H H H OCF₂CHF₂ i-Pr H H H SCF₂CHF₂ i-Pr H H H n-C₃F₇ i-Pr H H H i-C₃F₇ i-Pr H H H Br i-Pr H H H Cl i-Pr H H H SCF₃ i-Pr H H Me CF₃ i-Pr H H Me OCF₃ i-Pr H H Me OCHF₂ i-Pr H H Me C₂F₅ i-Pr H H Me OCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ i-Pr H H Me n-C₃F₇ i-Pr H H Me i-C₃F₇ i-Pr H H Me Br i-Pr H H Me Cl i-Pr H H Me SCF₃ i-Pr H H Me I i-Pr H H Me SMe i-Pr H H Me OMe i-Pr H H Me OEt i-Pr H H Me Et i-Pr H H Me SO₂Me i-Pr H H Me SO₂CF₃ i-Pr H H Et CF₃ i-Pr H H Et Br i-Pr H H Et Cl i-Pr H H Ph CF₃ i-Pr H H Ph Br i-Pr H H Ph Cl i-Pr H H 2-pyridyl CF₃ i-Pr H H 2-pyridyl Cl i-Pr H H 2-ClPh CF₃ i-Pr H H 2-ClPh OCF₃ i-Pr H H 2-ClPh SCHF₂ i-Pr H H 2-ClPh Br Me Me H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl Me Me H CF₃ Me Me Me H F CF₃ Me Me H Cl CF₃ Me Me H n-Pr CF₃ Me Me H i-Pr CF₃ Me Me H CF₃ CF₃ Me Me H OMe CF₃ Me Me H 2-BrPh CF₃ Me Me H 2-MePh CF₃ Me Me H 2-CNPh CF₃ Me Me H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2-pyridyl CF₃ Me Me H 3-Me-2-pyridyl CF₃ Et Me H H CF₃ Et Me H H C₂F₅ Et Me H H OCF₃ Et Me H Me CF₃ Et Me H Me C₂F₅ Et Me H Me OCF₃ Me Cl H H CF₃ i-Pr H H 2-ClPh Cl i-Pr H H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-Cl-2-pyridyl Br i-Pr H H 3-Cl-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Cl i-Pr H H CF₃ Me i-Pr H H F CF₃ i-Pr H H Cl CF₃ i-Pr H H n-Pr CF₃ i-Pr H H i-Pr CF₃ i-Pr H H CF₃ CF₃ i-Pr H H OMe CF₃ i-Pr H H 2-BrPh CF₃ i-Pr H H 2-MePh CF₃ i-Pr H H 2-CNPh CF₃ i-Pr H H 2-FPh CF₃ i-Pr H H 2,6-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ i-Pr H H 2-MeOPh CF₃ i-Pr H H 3-F-2-pyridyl CF₃ i-Pr H H 3-CF₃-2-pyridyl CF₃ i-Pr H H 3-Me-2-pyridyl CF₃ i-Pr Me H H CF₃ i-Pr Me H H C₂F₅ i-Pr Me H H OCF₃ i-Pr Me H Me CF₃ i-Pr Me H Me C₂F₅ i-Pr Me H Me OCF₃ Me Cl H 2-ClPh CF₃ Me Cl H H OCF₃ Me Cl H H OCHF₂ Me Cl H H C₂F₅ Me Cl H H OCF₂CHF₂ Me Cl H H SCF₂CHF₂ Me Cl H H n-C₃F₇ Me Cl H H i-C₃F₇ Me Cl H H Br Me Cl H H Cl Me Cl H H SCF₃ Me Cl H Me CF₃ Me Cl H Me OCF₃ Me Cl H Me OCHF₂ Me Cl H Me C₂F₅ Me Cl H Me OCF₂CHF₂ Me Cl H Me SCF₂CHF₂ Me Cl H Me n-C₃F₇ Me Cl H Me i-C₃F₇ Me Cl H Me Br Me Cl H Me Cl Me Cl H Me SCF₃ Me Cl H Me I Me Cl H Me SMe Me Cl H Me OMe Me Cl H Me OEt Me Cl H Me Et Me Cl H Me SO₂Me Me Cl H Me SO₂CF₃ Me Cl H Et CF₃ Me Cl H Et Br Me Cl H Et Cl Me Cl H Ph CF₃ Me Cl H Ph Br Me Cl H Ph Cl Me Cl H 2-pyridyl CF₃ Me Cl H 2-ClPh OCF₃ Me Cl H 2-ClPh SCHF₂ Me Cl H 2-ClPh Br Me Cl H 2-ClPh Cl Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H 3-Cl-2-pyridyl Br Me Cl H 3-Cl-2-pyridyl Cl Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H 3-Br-2-pyridyl Cl Me Cl H CF₃ Me Me Cl H F CF₃ Me Cl H Cl CF₃ Me Cl H n-Pr CF₃ Me Cl H i-Pr CF₃ Me Cl H CF₃ CF₃ Me Cl H OMe CF₃ Me Cl H 2-BrPh CF₃ Me Cl H 2-MePh CF₃ Me Cl H 2-CNPh CF₃ Me Cl H 2-FPh CF₃ Me Cl H 2,6-F₂Ph CF₃ Me Cl H 2,4-F₂Ph CF₃ Me Cl H 2,5-F₂Ph CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H 3-CF₃-2-pyridyl CF₃ Me Cl H 3-Me-2-pyridyl CF₃ Et Cl H H OCF₃ Et Cl H H C₂F₅ Et Cl H Me CF₃ Et Cl H Me C₂F₅ Me Cl H 2-pyridyl Cl i-Pr Cl H Me CF₃

TABLE 4

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H H H CF₃ Me H Me H OCF₃ Me H H H OCF₃ Me H Me Me CF₃ Me H H Me CF₃ Me H Me Me OCF₃ Me H H Me OCF₃ Me H Me Me OCHF₂ Me H H Me OCHF₂ Me H Me Me C₂F₅ Me H H Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H H Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Br Me H H Me Br Me H Me Me Cl Me H H Me Cl Me H Me Me SCF₃ Me H H Me SCF₃ Me H Me Me I Me H H Me I Me H Me Me SMe Me H H Me SMe Me H Me Me OMe Me H H Me OMe Me H Me Me QEt Me H H Me QEt Me H Me Me Et Me H H Me Et Me H Me Me SO₂Me Me H H Me SO₂Me Me H Me Me SO₂CF₃ Me H H Me SO₂CF₃ Me H Me Et CF₃ Me H H Et CF₃ Me H Me Et Br Me H H Et Br Me H Me Et Cl Me H H Et Cl Me H Me Ph CF₃ Me H H Ph CF₃ Me H Me Ph Br Me H H Ph Br Me H Me Ph Cl Me H H Ph Cl Me H Me 2-pyridyl CF₃ Me H H 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H H 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H H 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H H 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H H 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H H 2-ClPh Br Me H Me 2-ClPh Cl Me H H 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H H 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H H 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H H CF₃ Me Me H Me n-Pr CF₃ Me H H n-Pr CF₃ Me H Me i-Pr CF₃ Me H H i-Pr CF₃ Me H Me CF₃ CF₃ Me H H CF₃ CF₃ Me H Me OMe CF₃ Me H H OMe CF₃ Me H Me 2-BrPh CF₃ Me H H 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H H 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H H 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H H 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-CF3-2- CF₃ Me H H 3-CF₃-2- CF₃ pyridyl pyridyl Me H Me 3-Me-2- CF₃ Me H H 3-Me-2- CF₃ pyridyl pyridyl Et H Me Me CF₃ Et H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ Et H Me Me OCF₃ Et H H Me OCF₃ Me Me H Me C₂F₅ i-Pr H H Me C₂F₅ Me Me H Me OCF₂CHF₂ i-Pr H H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ i-Pr H H Me n-C₃F₇ Me Me H Me i-C₃F₇ i-Pr H H Me i-C₃F₇ Me Me H Me Br i-Pr H H Me Br Me Me H Me Cl i-Pr H H Me Cl Me Me H Me SCF₃ i-Pr H H Me SCF₃ Me Me H Me I i-Pr H H Me I Me Me H Me SMe i-Pr H H Me SMe Me Me H Me OMe i-Pr H H Me OMe Me Me H Me OEt i-Pr H H Me OEt Me Me H Me Et i-Pr H H Me Et Me Me H Me SO₂Me i-Pr H H Me SO₂Me Me Me H Me SO₂CF₃ i-Pr H H Me SO₂CF₃ Me Me H Et CF₃ i-Pr H H Et CF₃ Me Me H Et Br i-Pr H H Et Br Me Me H Et Cl i-Pr H H Et Cl Me Me H Ph CF₃ i-Pr H H Ph CF₃ Me Me H Ph Br i-Pr H H Ph Br Me Me H Ph Cl i-Pr H H Ph Cl Me Me H 2-pyridyl CF₃ i-Pr H H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl i-Pr H H 2-pyridyl Cl Me Me H 2-ClPh CF₃ i-Pr H H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ i-Pr H H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ i-Pr H H 2-ClPh SCHF₂ Me Me H 2-ClPh Br i-Pr H H 2-ClPh Br Me Me H 2-ClPh Cl i-Pr H H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br i-Pr H H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl i-Pr H H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl Cl Me Me H CF₃ Me f-Pr H H CF₃ Me Me Me H n-Pr CF₃ i-Pr H H n-Pr CF₃ Me Me H i-Pr CF₃ i-Pr H H i-Pr CF₃ Me Me H CF₃ CF₃ i-Pr H H CF₃ CF₃ Me Me H 2-BrPh CF₃ i-Pr H H 2-BrPh CF₃ Me Me H 2-MePh CF₃ i-Pr H H 2-MePh CF₃ Me Me H 2-CNPh CF₃ i-Pr H H 2-CNPh CF₃ Me Me H 2-FPh CF₃ i-Pr H H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ i-Pr H H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ i-Pr H H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ i-Pr H H 3-F-2-pyridyl CF₃ Me Me H 3-CF3-2- CF₃ i-Pr H H 3-CF3-2- CF₃ pyridyl pyridyl Me Me H 3-Me-2- CF₃ i-Pr H H 3-Me-2- CF₃ pyridyl pyridyl Et Me H Me CF₃ i-Pr Me H Me CF₃ Et Me H Me C₂F₅ i-Pr Me H Me C₂F₅ Et Me H Me OCF₃ i-Pr Me H Me OCF₃ Me Cl H Me CF₃ Me Cl H 2-ClPh Br Me Cl H Me OCF₃ Me Cl H 2-ClPh Cl Me Cl H Me OCHF₂ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H Me C₂F₅ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H Me OCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H Me SCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl Br Me Cl H Me n-C₃F₇ Me Cl H 3-Cl-2-pyridyl Cl Me Cl H Me i-C₃F₇ Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H Me Br Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H Me Cl Me Cl H 3-Br-2-pyridyl Br Me Cl H Me SCF₃ Me Cl H 3-Br-2-pyridyl Cl Me Cl H Me I Me Cl H CF₃ Me Me Cl H Me SMe Me Cl H n-Pr CF₃ Me Cl H Me OMe Me Cl H i-Pr CF₃ Me Cl H Me OEt Me Cl H CF₃ CF₃ Me Cl H Me Et Me Cl H 2-BrPh CF₃ Me Cl H Me SO₂Me Me Cl H 2-MePh CF₃ Me Cl H Me SO₂CF₃ Me Cl H 2-CNPh CF₃ Me Cl H Et CF₃ Me Cl H 2-FPh CF₃ Me Cl H Et Br Me Cl H 2,6-F₂Ph CF₃ Me Cl H Et Cl Me Cl H 2,4-F₂Ph CF₃ Me Cl H Ph CF₃ Me Cl H 2,5-F₂Ph CF₃ Me Cl H Ph Br Me Cl H 2-MeOPh CF₃ Me Cl H Ph Cl Me Cl H 3-F-2-pyridyl CF₃ Me Cl H 2-pyridyl CF₃ Me Cl H 3-CF₃₋₂₋ CF₃ pyridyl Me Cl H 2-pyridyl Cl Me Cl H 3-Me-2- CF₃ pyridyl Me Cl H 2-ClPh CF₃ Et Cl H Me CF₃ Me Cl H 2-ClPh OCF₃ Et Cl H Me C₂F₅ Me Cl H 2-ClPh SCHF₂ i-Pr Cl H Me CF₃

TABLE 5

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CHF₂ Me H H H CHF₂ Me H Me H CH₂CF₃ Me H H H CH₂CF₃ Et H Me H CH₂CF₃ Et H H H CH₂CF₃ Me H Me Me CH₂CF₃ Me H H Me CH₂CF₃ Me H Me Et CH₂CF₃ Me H H Et CH₂CF₃ Me H Me Me CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me Et CHF₂ Me H H Et CHF₂ Me H Me Me CHF₂ Me H H Me CHF₂ Me H Me Me CBrF₂ Me H H Me CBrF₂ Me H Me Me CHF₂ Me H H Me CHF₂ Et H Me Me CH₂CF₃ Et H H Me CH₂CF₃ Me H Me Me Et Me H H Me Et Me H Me Me n-Pr Me H H Me n-Pr Me H Me Me CH₂C₂F₅ Me H H Me CH₂C₂F₅ n-Pr H Me Me CH₂CF₃ n-Pr H H Me CH₂CF₃ Me H Me Me CF₃ Me H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ Me H Me Et CHF₂ Me H H Et CHF₂ Me H Me n-Pr CH₂CF₃ Me H H n-Pr CH₂CF₃ Me H Me i-Pr CHF₂ Me H H i-Pr CHF₂ Me H Me Cl CH₂CF₃ Me H H Cl CH₂CF₃ Me H Me F CH₂CF₃ Me H H F CH₂CF₃ Me H Me Me CH₂Cl Me H H Me CH₂Cl Me H Me Me CClF₂ Me H H Me CClF₂ Me H Me Me CH₂CH₂Cl Me H H Me CH₂CH₂Cl Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Allyl Me H H Me Allyl Me H Me Et CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me Et i-C₃F₇ Me H H Me i-C₃F₇ Me H Me i-Pr CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me n-Pr CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me CF₃ CF₂CHF₂ Me H H CF₃ CF₂CHF₂ Me H Me CF₃ Me Me H H CF₃ Me Me H Me OMe CH₂CF₃ Me H H OMe CH₂CF₃ Me H Me H CH₂CF₃ Me H H H CH₂CF₃ Me H Me H CH₂CF₃ Me H H H CH₂CF₃ Me H Me H C₂F₅ Me H H H C₂F₅ Et H Me H C₂F₅ Et H H H C₂F₅ Me H Me H C₂F₅ Me H H H C₂F₅ Me H Me H CF₂CHF₂ Me H H H CF₂CHF₂ Me H Me i-Pr CH₂CF₃ Me H H H CH₂CF₃ Me H Me H n-C₃F₇ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H H H i-C₃F₇ Me H Me Ph CH₂CF₃ Me H H H CH₂CF₃ Me H Me Ph CF₂CHF₂ Me H H H CF₂CHF₂ Me H Me Ph CHF₂ Me H H H CHF₂ Me H Me 2-pyridyl CH₂CF₃ Me H H Ph CH₂CF₃ Me H Me 2-pyridyl CF₂CHF₂ Me H H Ph CF₂CHF₂ Me H Me 2-ClPh CH₂CF₃ Me H H Ph CH₂CF₃ Me H Me 2-ClPh CF₂CHF₂ Me H H 2-pyridyl CF₂CHF₂ Me H Me 2-ClPh CHF₂ Me H H 2-pyridyl CHF₂ Me H Me 2-ClPh Et Me H H 2-ClPh Et Me H Me 2-ClPh CBrF₂ Me H H 2-ClPh CBrF₂ Me H Me 2-BrPh CH₂CF₃ Me H H 2-ClPh CH₂CF₃ Me H Me 2-MePh CH₂CF₃ Me H H 2-ClPh CH₂CF₃ Me H Me 2-CNPh CH₂CF₃ Me H H 2-ClPh CH₂CF₃ Me H Me 2-FPh CH₂CF₃ Me H H 2-BrPh CH₂CF₃ Me H Me 2,6-F₂Ph CH₂CF₃ Me H H 2-MePh CH₂CF₃ Me H Me 2,4-F₂Ph CH₂CF₃ Me H H 2-CNPh CH₂CF₃ Me H Me 2,5-F₂Ph CH₂CF₃ Me H H 2-FPh CH₂CF₃ Me H Me 2-MeOPh CH₂CF₃ Me H H 2,6-F₂Ph CH₂CF₃ Me H Me 3-Cl-2-pyridyl CH₂CF₃ Me H H 2,4-F₂Ph CH₂CF₃ Me H Me 3-Cl-2-pyridyl CF₂CHF₂ Me H H 2,5-FP₂Ph CF₂CHF₂ Me H Me 3-Cl-2-pyridyl CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-Cl-2-pyridyl CHF_(2J) Me H H 3-Cl-2-pyridyl CHF₂ Me H Me 3-Cl-2-pyridyl CBrF₂ Me H H 3-Cl-2-pyridyl CBrF₂ Me H Me 3-F-2-pyridyl CH₂CF₃ Me H H 3-Cl-2-pyridyl CH₂CF₃ Me H Me 3-CF₃-2- CH₂CF₃ Me H H 3-CF₃-2- CH₂CF₃ pyridyl pyridyl Me H Me 3-Me-2- CH₂CF₃ Me H H 3-Me-2- CF₂CHF₂ pyridyl pyridyl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl CH₂CF₃ Me H H 3-Cl-2-pyridyl CH₂CF₃ Me H Me 3-Br-2-pyridyl CF₂CHF₂ Me H H 3-Cl-2-pyridyl CH₂CF₃ Me H Me 3-Br-2-pyridyl CClF₂ Me H H 3-Br-2-pyridyl CClF₂ Me Me H H CHF₂ Me H H 3-Br-2-pyridyl CH₂CF₃ Me Me H H CH₂CF₃ Me H H 3-Br-2-pyiidyl CF₃ Et Me H H CH₂CF₃ Me H H 3-Br-2-pyridyl CF₃ Me Me H Me CH₂CF₃ i-Pr H H Et CH₂C₂F₅ Me Me H Et CH₂CF₃ i-Pr H H n-Pr CH₂CF₃ Me Me H Me CF₂CHF₂ i-Pr H H i-Pr CF₃ Me Me H Et CHF₂ i-Pr H H Cl C₂F₅ Me Me H Me CHF₂ i-Pr H H F CHF₂ Me Me H Me CBrF₂ i-Pr H H Me CH₂CF₃ Me Me H Me CHF₂ i-Pr H H Me CHF₂ Et Me H Me CH₂CF₃ i-Pr H H Me CH₂CF₃ Me Me H Me Et i-Pr H H Me CH₂CF₃ Me Me H Me n-Pr i-Pr H H Me CH₂Cl Me Me H Me CH₂C₂F₅ i-Pr H H Me CClF₂ n-Pr Me H Me CH₂CF3i-Pr H H Me CH₂CH₂Cl Me Me H Me CF₃ i-Pr H H Me n-C₃F₇ Et Me H Me C₂F₅ i-Pr H H Me i-C₃F₇ Me Me H Et CHF₂ i-Pr H H Me Allyl Me Me H n-Pr CH₂CF₃ i-Pr H H CF₃ CF₂CHF₂ Me Me H i-Pr CHF₂ i-Pr H H CF₃ i-C₃F₇ Me Me H Cl CH₂CF₃ i-Pr H H OMe CF₂CHF₂ Me Me H F CH₂CF₃ i-Pr H H H CF₂CHF₂ Me Me H Me CH₂Cl i-Pr H H H CF₂CHF₂ Me Me H Me CClF₂ i-Pr H H H Me Me Me H Me CH₂CH₂Cl i-Pr H H H CH₂CF₃ Me Me H Me n-C₃F₇ i-Pr H H H CH₂CF₃ Me Me H Me i-C₃F₇ i-Pr H H H C₂F₅ Me Me H Me Allyl i-Pr H H H C₂F₅ Me Me H Me CF₂CHF₂ i-Pr H H H C₂F₅ Me Me H Me i-C₃F₇ i-Pr H H H CF₂CHF₂ Me Me H Me CF₂CHF₂ i-Pr H H H CH₂CF₃ Me Me H Me CF₂CHF₂ i-Pr H H H n-C₃F₇ Me Me H CF₃ CF₂CHF₂ i-Pr H H Ph i-C₃F₇ Me Me H CF₃ Me i-Pr H H Ph CH₂CF₃ Me Me H OMe CH₂CF₃ i-Pr H H Ph CF₂CHF₂ Me Me H H CH₂CF₃ i-Pr H H 2-pyridyl CHF₂ Me Me H H CH₂CF₃ i-Pr H H 2-pyridyl CH₂CF₃ Me Me H H C₂F₅ i-Pr H H 2-ClPh CF₂CHF₂ Et Me H H C₂F₅ i-Pr H H 2-ClPh CH₂CF₃ Me Me H H C₂F₅ i-Pr H H 2-ClPh CF₂CHF₂ Me Me H H CF₂CHF₂ i-Pr H H 2-ClPh CHF₂ Me Me H H CH₂CF₃ i-Pr H H 2-ClPh Et Me Me H H n-C₃F₇ i-Pr H H 2-BrPh CBrF₂ Me Me H H i-C₃F₇ i-Pr H H 2-MePh CH₂CF₃ Me Me H H CH₂CF₃ i-Pr H H 2-CNPh CH₂CF₃ Me Me H H CF₂CHF₂ i-Pr H H 2-FPh CH₂CF₃ Me Me H H CHF₂ i-Pr H H 2,6-F₂Ph CH₂CF₃ Me Me H Ph CH₂CF₃ i-Pr H H 2,4-F₂Ph CH₂CF₃ Me Me H Ph CF₂CHF₂ i-Pr H H 2,5-F₂Ph CH₂CF₃ Me Me H Ph CH₂CF₃ i-Pr H H 2-MeOPh CH₂CF₃ Me Me H 2-pyridyl CF₂CHF₂ i-Pr H H 3-Cl-2-pyridyl CH₂CF₃ Me Me H 2-pyridyl CHF₂ i-Pr H H 3-Cl-2-pyridyl CH₂CF₃ Me Me H 2-ClPh Et i-Pr H H 3-Cl-2-pyridyl CF₂CHF₂ Me Me H 2-ClPh CBrF₂ i-Pr H H 3-Cl-2-pyridyl CF₃ Me Me H 2-ClPh CH₂CF₃ i-Pr H H 3-Cl-2-pyridyl CHF₂ Me Me H 2-ClPh CH₂CF₃ i-Pr H H 3-F-2-pyridyl CBrF₂ Me Me H 2-ClPh CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CH₂CF₃ Me Me H 2-BrPh CH₂CF₃ i-Pr H H 3-CF₃-2- CH₂CF₃ pyridyl Me Me H 2-MePh CH₂CF₃ i-Pr H H 3-Me-2- CH₂CF₃ pyridyl Me Me H 2-CNFh CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CF₃ Me Me H 2-FPh CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CH₂CF₃ Me Me H 2,6-F₂Ph CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CF₂CHF₂ Me Me H 2,4-F₂Ph CH₂CF₃ Me Cl H F CH₂CF₃ Me Me H 2,5-F₂Ph CF₂CHF₂ Me Cl H Me CHF₂ Me Me H 2-MeOPh CF₃ Me Cl H Me CH₂CF₃ Me Me H 3-Cl-2-pyridyl CHF₂ Me Cl H Me CH₂CF₃ Me Me H 3-Cl-2-pyridyl CBrF₂ Me Cl H Me CH₂Cl Me Me H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H Me CClF₂ Me Me H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H Me CH₂CH₂Cl Me Me H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H Me n-C₃F₇ Me Me H 3-F-2-pyridyl CF3 Me Cl H Me i-C₃F₇ Me Me H 3-CF₃-2- CH₂CF₃ Me Cl H Me Allyl pyridyl Me Me H 3-Me-2- CF₂CHF₂ Me Cl H Me CF₂CHF₂ pyridyl Me Me H 3-Br-2-pyridyl CClF₂ Me Cl H CF₃ i-C₃F₇ Me Me H 3-Br-2-pyridyl CH₂CF₃ Me Cl H CF₃ CF₂CHF₂ Me Me H 3-Br-2-pyridyl CF₃ Me Cl H OMe CF₂CHF₂ Me Me H 3-Br-2-pyridyl CF₃ Me Cl H H CF₂CHF₂ Me Cl H Me CHF₂ Me Cl H H Me Me Cl H Et CH₂CF₃ Me Cl H H CH₂CF₃ Me Cl H Me CH₂CF₃ Et Cl H H CH₂CF₃ Me Cl H Et CH₂CF₃ Me Cl H H CH₂CF₃ Me Cl H Me CH₂CF₃ Me Cl H H C₂F₅ Me Cl H Me CF₂CHF₂ Me Cl H H C₂F₅ Me Cl H Me CHF₂ Me Cl H H C₂F₅ Et Cl H Me CHF₂ Me Cl H H CF₂CHF₂ Me Cl H Me CBrF₂ Me Cl H H CH₂CF₃ Me Cl H Me CHF₂ Me Cl H H n-C₃F₇ Me Cl H Me CH₂CF₃ Me Cl H 3-Me-2- CH₂CF₃ pyridyl n-Pr Cl H Me Et Me Cl H H i-C₃F₇ Me Cl H Me n-Pr Me Cl H Ph CH₂CF₃ Et Cl H Me CH₂C₂F₅ Me Cl H Ph CF₂CHF₂ Me Cl H Et CH₂CF₃ Me Cl H Ph CHF₂ Me Cl H n-Pr CF₃ Me Cl H 2-pyridyl CH₂CF₃ Me Cl H i-Pr C₂F₅ Me Cl H 2-pyridyl CF₂CHF₂ Me Cl H Cl CHF₂ Me Cl H 2-ClPh CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H 2-ClPh CF₂CHF₂ Me Cl H 3-Cl-2-pyridyl CF₂CHF₂ Me Cl H 2-FPh CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H 2,6-F₂Ph CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CHF₂ Me Cl H 2,4-F₂Ph CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CBrF₂ Me Cl H 2-ClPh Et Me Cl H 3-F-2-pyridyl CH₂CF₃ Me Cl H 2-ClPh CBrF₂ Me Cl H 3-CF₃-2- CH₂CF₃ Me Cl H 2-BrPh CH₂CF₃ pyridyl Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H 2-MePh CH₂CF₃ Me Cl H 3-Br-2-pyridyl CH₂CF₃ Me Cl H 2-CNPh CH₂CF₃ Me Cl H 3-Br-2-pyridyl CF₂CHF₂ Me Cl H 2-MeOPh CH₂CF₃ Me Cl H 3-Br-2-pyridyl CClF₂ Me Cl H 2,5-F₂Ph CH₂CF₃ Me Cl H 2-ClPh CHF₂

TABLE 6

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H H H CF₃ Me H Me H OCF₃ Me H H H OCF₃ Me H Me H OCHF₂ Me H H H OCHF₂ Me H Me H C₂F₅ Me H H H C₂F₅ Me H Me H OCF₂CHF₂ Me H H H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H H H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H H H i-C₃F₇ Me H Me H Br Me H H H Br Me H Me H Cl Me H H H Cl Me H Me H SCF₃ Me H H H SCF₃ Me H Me Me CF₃ Me H H Me CF₃ Me H Me Me OCF₃ Me H H Me OCF₃ Me H Me Me OCHF₂ Me H H Me OCHF₂ Me H Me Me C₂F₅ Me H H Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H H Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Br Me H H Me Br Me H Me Me Cl Me H H Me Cl Me H Me Me SCF₃ Me H H Me SCF₃ Me H Me Me I Me H H Me I Me H Me Me SMe Me H H Me SMe Me H Me Me OMe Me H H Me OMe Me H Me Me OEt Me H H Me OEt Me H Me Me Et Me H H Me Et Me H Me Me SO₂Me Me H H Me SO₂Me Me H Me Me SO₂CF₃ Me H H Me SO₂CF₃ Me H Me Et CF₃ Me H H Et CF₃ Me H Me Et Br Me H H Et Br Me H Me Et Cl Me H H Et Cl Me H Me Ph CF₃ Me H H Ph CF₃ Me H Me Ph Br Me H H Ph Br Me H Me Ph Cl Me H H Ph Cl Me H Me 2-pyridyl CF₃ Me H H 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H H 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H H 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H H 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H H 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H H 2-ClPh Br Me H Me 2-ClPh Cl Me H H 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H H 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H H 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H H CF₃ Me Me H Me F CF₃ Me H H F CF₃ Me H Me Cl CF₃ Me H H Cl CF₃ Me H Me n-Pr CF₃ Me H H n-Pr CF₃ Me H Me i-Pr CF₃ Me H H i-Pr CF₃ Me H Me CF₃ CF₃ Me H H CF₃ CF₃ Me H Me OMe CF₃ Me H H OMe CF₃ Me H Me 2-BrPh CF₃ Me H H 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H H 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H H 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H H 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2- CF₃ Me H H 3-CF₃-2- CF₃ pyridyl pyridyl Me H Me 3-Me-2- CF₃ Me H H 3-Me-2- CF₃ pyridyl pyridyl Et H Me H CF₃ Et H H H CF₃ Et H Me H C₂F₅ Et H H H C₂F₅ Et H Me H OCF₃ Et H H H OCF₃ Et H Me Me CF₃ Et H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ Et H Me Me OCF₃ Et H H Me OCF₃ Me Me H H CF₃ i-Pr H H H CF₃ Me Me H H OCF₃ i-Pr H H H OCF₃ Me Me H H OCHF₂ i-Pr H H H OCHF₂ Me Me H H C₂F₅ i-Pr H H H C₂F₅ Me Me H H OCF₂CHF₂ i-Pr H H H OCF₂CHF₂ Me Me H H SCF₂CHF₂ i-Pr H H H SCF₂CHF₂ Me Me H H n-C₃F₇ i-Pr H H H n-C₃F₇ Me Me H H i-C₃F₇ i-Pr H H H i-C₃F₇ Me Me H H Br i-Pr H H H Br Me Me H H Cl i-Pr H H H Cl Me Me H H SCF₃ i-Pr H H H SCF₃ Me Me H H CF₃ i-Pr H H Me CF₃ Me Me H H OCF₃ i-Pr H H Me OCF₃ Me Me H H OCHF₂ i-Pr H H Me OCHF₂ Me Me H Me C₂F₅ i-Pr H H Me C₂F₅ Me Me H Me OCF₂CHF₂ i-Pr H H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ i-Pr H H Me n-C₃F₇ Me Me H Me i-C₃F₇ i-Pr H H Me i-C₃F₇ Me Me H Me Br i-Pr H H Me Br Me Me H Me Cl i-Pr H H Me Cl Me Me H Me SCF₃ i-Pr H H Me SCF₃ Me Me H Me I i-Pr H H Me I Me Me H Me SMe i-Pr H H Me SMe Me Me H Me OMe i-Pr H H Me OMe Me Me H Me OEt i-Pr H H Me OEt Me Me H Me Et i-Pr H H Me Et Me Me H Me SO₂Me i-Pr H H Me SO₂Me Me Me H Me SO₂CF₃ i-Pr H H Me SO₂CF₃ Me Me H Et CF₃ i-Pr H H Et CF₃ Me Me H Et Br i-Pr H H Et Br Me Me H Et Cl i-Pr H H Et Cl Me Me H Ph CF₃ i-Pr H H Ph CF₃ Me Me H Ph Br i-Pr H H Ph Br Me Me H Ph Cl i-Pr H H Ph Cl Me Me H 2-pyridyl CF₃ i-Pr H H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl i-Pr H H 2-pyridyl Cl Me Me H 2-ClPh CF₃ i-Pr H H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ i-Pr H H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ i-Pr H H 2-ClPh SCHF₂ Me Me H 2-ClPh Br i-Pr H H 2-ClPh Br Me Me H 2-ClPh Cl i-Pr H H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br i-Pr H H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl i-Pr H H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl Cl Me Me H CF₃ Me i-Pr H H CF₃ Me Me Me H F CF₃ i-Pr H H F CF₃ Me Me H Cl CF₃ i-Pr H H Cl CF₃ Me Me H n-Pr CF₃ i-Pr H H n-Pr CF₃ Me Me H i-Pr CF₃ i-Pr H H i-Pr CF₃ Me Me H CF₃ CF₃ i-Pr H H CF₃ CF₃ Me Me H OMe CF₃ i-Pr H H OMe CF₃ Me Me H 2-BrPh CF₃ i-Pr H H 2-BrPh CF₃ Me Me H 2-MePh CF₃ i-Pr H H 2-MePh CF₃ Me Me H 2-CNPh CF₃ i-Pr H H 2-CNPh CF₃ Me Me H 2-FPh CF₃ i-Pr H H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ i-Pr H H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ i-Pr H H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ i-Pr H H 3-F-2-pyridyl CF₃ Me Me H 3-CF3-2- CF₃ i-Pr H H 3-CF₃-2- CF₃ pyridyl pyridyl Me Me H 3-Me-2- CF₃ i-Pr H H 3-Me-2- CF₃ pyridyl pyridyl Et Me H H CF₃ i-Pr Me H H CF₃ Et Me H H C₂F₅ i-Pr Me H H C₂F₅ Et Me H H OCF₃ i-Pr Me H H OCF₃ Et Me H Me CF₃ i-Pr Me H Me CF₃ Et Me H Me C₂F₅ i-Pr Me H Me C₂F₅ Et Me H Me OCF₃ i-Pr Me H Me OCF₃ Me Cl H H CF₃ Me Cl H 2-ClPh CF₃ Me Cl H H OCF₃ Me Cl H 2-ClPh OCF₃ Me Cl H H OCHF₂ Me Cl H 2-ClPh SCHF₂ Me Cl H H C₂F₅ Me Cl H 2-ClPh Br Me Cl H H OCF₂CHF₂ Me Cl H 2-ClPh Cl Me Cl H H SCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H H n-C₃F₇ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H H i-C₃F₇ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H H Br Me Cl H 3-Cl-2-pyridyl Br Me Cl H H Cl Me Cl H 3-Cl-2-pyridyl Cl Me Cl H H SCF₃ Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H Me CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H Me OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H Me OCHF₂ Me Cl H 3-Br-2-pyridyl Cl Me Cl H Me C₂F₅ Me Cl H CF₃ Me Me Cl H Me OCF₂CHF₂ Me Cl H F CF₃ Me Cl H Me SCF₂CHF₂ Me Cl H Cl CF₃ Me Cl H Me n-C₃F₇ Me Cl H n-Pr CF₃ Me Cl H Me i-C₃F₇ Me Cl H i-Pr CF₃ Me Cl H Me Br Me Cl H CF₃ CF₃ Me Cl H Me Cl Me Cl H OMe CF₃ Me Cl H Me SCF₃ Me Cl H 2-BrPh CF₃ Me Cl H Me I Me Cl H 2-MePh CF₃ Me Cl H Me SMe Me Cl H 2-CNPh CF₃ Me Cl H Me OMe Me Cl H 2-FPh CF₃ Me Cl H Me OEt Me Cl H 2,6-F₂Ph CF₃ Me Cl H Me Et Me Cl H 2,4-F₂Ph CF₃ Me Cl H Me SO₂Me Me Cl H 2,5-F₂Ph CF₃ Me Cl H Me SO₂CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H Et CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H Et Br Me Cl H 3-CF₃-2- CF₃ pyridyl Me Cl H Et Cl Me Cl H 3-Me-2- CF₃ pyridyl Me Cl H Ph CF₃ Et Cl H H OCF₃ Me Cl H Ph Br Et Cl H H C₂F₅ Me Cl H Ph Cl Et Cl H Me CF₃ Me Cl H 2-pyridyl CF₃ Et Cl H Me C₂F₅ Me Cl H 2-pyridyl Cl i-Pr Cl H Me CF₃

TABLE 7

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H H H CF₃ Me H Me H OCF₃ Me H H H OCF₃ Me H Me H OCHF₂ Me H H H OCHF₂ Me H Me H C₂F₅ Me H H H C₂F₅ Me H Me H OCF₂CHF₂ Me H H H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H H H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H H H i-C₃F₇ Me H Me H Br Me H H H Br Me H Me H Cl Me H H H Cl Me H Me H SCF₃ Me H H H SCF₃ Me H Me Me CF₃ Me H H Me CF₃ Me H Me Me OCF₃ Me H H Me OCF₃ Me H Me Me OCHF₂ Me H H Me OCHF₂ Me H Me Me C₂F₅ Me H H Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H H Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Br Me H H Me Br Me H Me Me Cl Me H H Me Cl Me H Me Me SCF₃ Me H H Me SCF₃ Me H Me Me I Me H H Me I Me H Me Me SMe Me H H Me SMe Me H Me Me OMe Me H H Me OMe Me H Me Me OEt Me H H Me OEt Me H Me Me Et Me H H Me Et Me H Me Me SO₂Me Me H H Me SO₂Me Me H Me Me SO₂CF₃ Me H H Me SO₂CF₃ Me H Me Et CF₃ Me H H Et CF₃ Me H Me Et Br Me H H Et Br Me H Me Et Cl Me H H Et Cl Me H Me Ph CF₃ Me H H Ph CF₃ Me H Me Ph Br Me H H Ph Br Me H Me Ph Cl Me H H Ph Cl Me H Me 2-pyridyl CF₃ Me H H 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H H 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H H 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H H 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H H 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H H 2-ClPh Br Me H Me 2-ClPh Cl Me H H 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H H 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H H 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H H CF₃ Me Me H Me F CF₃ Me H H F CF₃ Me H Me Cl CF₃ Me H H Cl CF₃ Me H Me n-Pr CF₃ Me H H n-Pr CF₃ Me H Me i-Pr CF₃ Me H H i-Pr CF₃ Me H Me CF₃ CF₃ Me H H CF₃ CF₃ Me H Me OMe CF₃ Me H H OMe CF₃ Me H Me 2-BrPh CF₃ Me H H 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H H 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H H 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H H 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2- CF₃ Me H H 3-CF₃-2- CF₃ pyridyl pyridyl Me H Me 3-Me-2- CF₃ Me H H 3-Me-2- CF₃ pyridyl pyridyl Et H Me H CF₃ Et H H H CF₃ Et H Me H C₂F₅ Et H H H C₂F₅ Et H Me H OCF₃ Et H H H OCF₃ Et H Me Me CF₃ Et H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ Et H Me Me OCF₃ Et H H Me OCF₃ Me Me H H CF₃ i-Pr H H H CF₃ Me Me H H OCF₃ i-Pr H H H OCF₃ Me Me H H OCHF₂ i-Pr H H H OCHF₂ Me Me H H C₂F₅ i-Pr H H H C₂F₅ Me Me H H OCF₂CHF₂ i-Pr H H H OCF₂CHF₂ Me Me H H SCF₂CHF₂ i-Pr H H H SCF₂CHF₂ Me Me H H n-C₃F₇ i-Pr H H H n-C₃F₇ Me Me H H i-C₃F₇ i-Pr H H H i-C₃F₇ Me Me H H Br i-Pr H H H Br Me Me H H Cl i-Pr H H H Cl Me Me H H SCF₃ i-Pr H H H SCF₃ Me Me H H CF₃ i-Pr H H Me CF₃ Me Me H H OCF₃ i-Pr H H Me OCF₃ Me Me H H OCHF₂ i-Pr H H Me OCHF₂ Me Me H Me C₂F₅ i-Pr H H Me C₂F₅ Me Me H Me OCF₂CHF₂ i-Pr H H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ i-Pr H H Me n-C₃F₇ Me Me H Me i-C₃F₇ i-Pr H H Me i-C₃F₇ Me Me H Me Br i-Pr H H Me Br Me Me H Me Cl i-Pr H H Me Cl Me Me H Me SCF₃ i-Pr H H Me SCF₃ Me Me H Me I i-Pr H H Me I Me Me H Me SMe i-Pr H H Me SMe Me Me H Me OMe i-Pr H H Me OMe Me Me H Me OEt i-Pr H H Me OEt Me Me H Me Et i-Pr H H Me Et Me Me H Me SO₂Me i-Pr H H Me SO₂Me Me Me H Me SO₂CF₃ i-Pr H H Me SO₂CF₃ Me Me H Et CF₃ i-Pr H H Et CF₃ Me Me H Et Br i-Pr H H Et Br Me Me H Et Cl i-Pr H H Et Cl Me Me H Ph CF₃ i-Pr H H Pb CF₃ Me Me H Ph Br i-Pr H H Ph Br Me Me H Ph Cl i-Pr H H Ph Cl Me Me H 2-pyridyl CF₃ i-Pr H H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl i-Pr H H 2-pyridyl Cl Me Me H 2-ClPh CF₃ i-Pr H H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ i-Pr H H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ i-Pr H H 2-ClPh SCHF₂ Me Me H 2-ClPh Br i-Pr H H 2-ClPh Br Me Me H 2-ClPh Cl i-Pr H H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br i-Pr H H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl i-Pr H H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl Cl Me Me H CF₃ Me i-Pr H H CF₃ Me Me Me H F CF₃ i-Pr H H F CF₃ Me Me H Cl CF₃ i-Pr H H Cl CF₃ Me Me H n-Pr CF₃ i-Pr H H n-Pr CF₃ Me Me H i-Pr CF₃ i-Pr H H i-Pr CF₃ Me Me H CF₃ CF₃ i-Pr H H CF₃ CF₃ Me Me H OMe CF₃ i-Pr H H OMe CF₃ Me Me H 2-BrPh CF₃ i-Pr H H 2-BrPh CF₃ Me Me H 2-MePh CF₃ i-Pr H H 2-MePh CF₃ Me Me H 2-CNPh CF₃ i-Pr H H 2-CNPh CF₃ Me Me H 2-FPh CF₃ i-Pr H H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ i-Pr H H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ i-Pr H H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ i-Pr H H 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2- CF₃ i-Pr H H 3-CF₃-2- CF₃ pyridyl pyridyl Me Me H 3-Me-2- CF₃ i-Pr H H 3-Me-2- CF₃ pyridyl pyridyl Et Me H H CF₃ i-Pr Me H H CF₃ Et Me H H C₂F₅ i-Pr Me H H C₂F₅ Et Me H H OCF₃ i-Pr Me H H OCF₃ Et Me H Me CF₃ i-Pr Me H Me CF₃ Et Me H Me C₂F₅ i-Pr Me H Me C₂F₅ Et Me H Me OCF₃ i-Pr Me H Me OCF₃ Me Cl H H CF₃ Me Cl H 2-ClPh CF₃ Me Cl H H OCF₃ Me Cl H 2-ClPh OCF₃ Me Cl H H OCHF₂ Me Cl H 2-ClPh SCHF₂ Me Cl H H C₂F₅ Me Cl H 2-ClPh Br Me Cl H H OCF₂CHF₂ Me Cl H 2-ClPh Cl Me Cl H H SCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H H n-C₃F₇ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H H i-C₃F₇ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H H Br Me Cl H 3-Cl-2-pyridyl Br Me Cl H H Cl Me Cl H 3-Cl-2-pyridyl Cl Me Cl H H SCF₃ Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H Me CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H Me OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H Me OCHF₂ Me Cl H 3-Br-2-pyridyl Cl Me Cl H Me C₂F₅ Me Cl H CF₃ Me Me Cl H Me OCF₂CHF₂ Me Cl H F CF₃ Me Cl H Me SCF₂CHF₂ Me Cl H Cl CF₃ Me Cl H Me n-C₃F₇ Me Cl H n-Pr CF₃ Me Cl H Me i-C₃F₇ Me Cl H i-Pr CF₃ Me Cl H Me Br Me Cl H CF₃ CF₃ Me Cl H Me Cl Me Cl H OMe CF₃ Me Cl H Me SCF₃ Me Cl H 2-BrPh CF₃ Me Cl H Me I Me Cl H 2-MePh CF₃ Me Cl H Me SMe Me Cl H 2-CNPh CF₃ Me Cl H Me OMe Me Cl H 2-FPh CF₃ Me Cl H Me OEt Me Cl H 2,6-F₂Ph CF₃ Me Cl H Me El Me Cl H 2,4-F₂Ph CF₃ Me Cl H Me SO₂Me Me Cl H 2,5-F₂Ph CF₃ Me Cl H Me SO₂CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H Et CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H Et Br Me Cl H 3-CF₃-2- CF₃ pyridyl Me Cl H Et Cl Me Cl H 3-Me-2- CF₃ pyridyl Me Cl H Ph CF₃ Et Cl H H OCF₃ Me Cl H Ph Br Et Cl H H C₂F₅ Me Cl H Ph Cl Et Cl H Me CF₃ Me Cl H 2-pyridyl CF₃ Et Cl H Me C₂F₅ Me Cl H 2-pyridyl Cl i-Pr Cl H Me CF₃

TABLE 8

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H H H CF₃ Me H Me H OCF₃ Me H H H OCF₃ Me H Me H OCHF₂ Me H H H OCHF₂ Me H Me H C₂F₅ Me H H H C₂F₅ Me H Me H OCF₂CHF₂ Me H H H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H H H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H H H i-C₃F₇ Me H Me H Br Me H H H Br Me H Me H Cl Me H H H Cl Me H Me H SCF₃ Me H H H SCF₃ Me H Me Me CF₃ Me H H Me CF₃ Me H Me Me OCF₃ Me H H Me OCF₃ Me H Me Me OCHF₂ Me H H Me OCHF₂ Me H Me Me C₂F₅ Me H H Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H H Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Br Me H H Me Br Me H Me Me Cl Me H H Me Cl Me H Me Me SCF₃ Me H H Me SCF₃ Me H Me Me I Me H H Me I Me H Me Me SMe Me H H Me SMe Me H Me Me OMe Me H H Me OMe Me H Me Me OEt Me H H Me OEt Me H Me Me Et Me H H Me Et Me H Me Me SO₂Me Me H H Me SO₂Me Me H Me Me SO₂CF₃ Me H H Me SO₂CF₃ Me H Me Et CF₃ Me H H Et CF₃ Me H Me Et Br Me H H Et Br Me H Me Et Cl Me H H Et Cl Me H Me Ph CF₃ Me H H Ph CF₃ Me H Me Ph Br Me H H Ph Br Me H Me Ph Cl Me H H Ph Cl Me H Me 2-pyridyl CF₃ Me H H 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H H 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H H 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H H 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H H 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H H 2-ClPh Br Me H Me 2-ClPh Cl Me H H 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H H 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF3 Me H H 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF3 Me H H 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H H 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H H CF₃ Me Me H Me F CF₃ Me H H F CF₃ Me H Me Cl CF₃ Me H H Cl CF₃ Me H Me n-Pr CF₃ Me H H n-Pr CF₃ Me H Me i-Pr CF₃ Me H H i-Pr CF₃ Me H Me CF₃ CF₃ Me H H CF₃ CF₃ Me H Me OMe CF₃ Me H H OMe CF₃ Me H Me 2-BrPh CF₃ Me H H 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H H 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H H 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H H 2-EPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2- CF₃ Me H H 3-CF₃-2- CF₃ pyridyl pyridyl Me H Me 3-Me-2- CF₃ Me H H 3-Me-2- CF₃ pyridyl pyridyl Et H Me H CF₃ Et H H H CF₃ Et H Me H C₂F₅ Et H H H C₂F₅ Et H Me H OCF₃ Et H H H OCF₃ Et H Me Me CF₃ Et H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ Et H Me Me OCF₃ Et H H Me OCF₃ Me Me H H CF₃ i-Pr H H H CF₃ Me Me H H OCF₃ i-Pr H H H OCF₃ Me Me H H OCHF₂ i-Pr H H H OCHF₂ Me Me H H C₂F₅ i-Pr H H H C₂F₅ Me Me H H OCF₂CHF₂ i-Pr H H H OCF₂CHF₂ Me Me H H SCF₂CHF₂ i-Pr H H H SCF₂CHF₂ Me Me H H n-C₃F₇ i-Pr H H H n-C₃F₇ Me Me H H i-C₃F₇ i-Pr H H H i-C₃F₇ Me Me H H Br i-Pr H H H Br Me Me H H Cl i-Pr H H H Cl Me Me H H SCF₃ i-Pr H H H SCF₃ Me Me H H CF₃ i-Pr H H Me CF₃ Me Me H H OCF₃ i-Pr H H Me OCF₃ Me Me H H OCHF₂ i-Pr H H Me OCHF₂ Me Me H Me C₂F₅ i-Pr H H Me C₂F₅ Me Me H Me OCF₂CHF₂ i-Pr H H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ i-Pr H H Me n-C₃F₇ Me Me H Me i-C₃F₇ i-Pr H H Me i-C₃F₇ Me Me H Me Br i-Pr H H Me Br Me Me H Me Cl i-Pr H H Me Cl Me Me H Me SCF₃ i-Pr H H Me SCF₃ Me Me H Me I i-Pr H H Me I Me Me H Me SMe i-Pr H H Me SMe Me Me H Me OMe i-Pr H H Me OMe Me Me H Me OEt i-Pr H H Me OEt Me Me H Me Et i-Pr H H Me Et Me Me H Me SO₂Me i-Pr H H Me SO₂Me Me Me H Me SO₂CF₃ i-Pr H H Me SO₂CF₃ Me Me H Et CF₃ i-Pr H H Et CF₃ Me Me H Et Br i-Pr H H Et Br Me Me H Et Cl i-Pr H H Et Cl Me Me H Ph CF₃ i-Pr H H Ph CF₃ Me Me H Ph Br i-Pr H H Ph Br Me Me H Ph Cl i-Pr H H Ph Cl Me Me H 2-pyridyl CF₃ i-Pr H H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl i-Pr H H 2-pyridyl Cl Me Me H 2-ClPh CF₃ i-Pr H H 2-ClPh CF₃ Me Me H 2-CLPh OCF₃ i-Pr H H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ i-Pr H H 2-ClPh SCHF₂ Me Me H 2-CiPh Br i-Pr H H 2-ClPh Br Me Me H 2-ClPh Cl i-Pr H H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br i-Pr H H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl i-Pr H H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl Cl Me Me H CF₃ Me i-Pr H H CF₃ Me Me Me H F CF₃ i-Pr H H F CF₃ Me Me H Cl CF₃ i-Pr H H Cl CF₃ Me Me H n-Pr CF₃ i-Pr H H n-Pr CF₃ Me Me H i-Pr CF₃ i-Pr H H i-Pr CF₃ Me Me H CF₃ CF₃ i-Pr H H CF₃ CF₃ Me Me H OMe CF₃ i-Pr H H OMe CF₃ Me Me H 2-BrPh CF₃ i-Pr H H 2-BrPh CF₃ Me Me H 2-MePh CF₃ i-Pr H H 2-MePh CF₃ Me Me H 2-CNPh CF₃ i-Pr H H 2-CNPh CF₃ Me Me H 2-FPh CF₃ i-Pr H H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ i-Pr H H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ i-Pr H H 2-MeOPh CF₃ Me Me H 3-F-2-pyxidyl CF₃ i-Pr H H 3-F-2-pyridyl CF₃ Me Me H 3-CF3-2- CF₃ i-Pr H H 3-C_(F)3-2- CF₃ pyridyl pyridyl Me Me H 3-Me-2- CF₃ i-Pr H H 3-Me-2- CF₃ pyridyl pyridyl Et Me H H CF₃ i-Pr Me H H CF₃ Et Me H H C₂F₅ i-Pr Me H H C₂F₅ Et Me H H OCF₃ i-Pr Me H H OCF₃ Et Me H Me CF₃ i-Pr Me H Me CF₃ Et Me H Me C₂F₅ i-Pr Me H Me C₂F₅ Et Me H Me OCF₃ i-Pr Me H Me OCF₃ Me Cl H H CF₃ Me Cl H 2-ClPh CF₃ Me Cl H H OCF₃ Me Cl H 2-ClPh OCF₃ Me Cl H H OCHF₂ Me Cl H 2-ClPh SCHF₂ Me Cl H H C₂F₅ Me Cl H 2-ClPh Br Me Cl H H OCF₂CHF₂ Me Cl H 2-ClPh Cl Me Cl H H SCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H H n-C₃F₇ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H H i-C₃F₇ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H H Br Me Cl H 3-Cl-2-pyridyl Br Me Cl H H Cl Me Cl H 3-Cl-2-pyridyl Cl Me Cl H H SCF₃ Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H Me CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H Me OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H Me OCHF₂ Me Cl H 3-Br-2-pyridyl Cl Me Cl H Me C₂F₅ Me Cl H CF₃ Me Me Cl H Me OCF₂CHF₂ Me Cl H F CF₃ Me Cl H Me SCF₂CHF₂ Me Cl H Cl CF₃ Me Cl H Me n-C₃F₇ Me Cl H n-Pr CF₃ Me Cl H Me i-C₃F₇ Me Cl H i-Pr CF₃ Me Cl H Me Br Me Cl H CF₃ CF₃ Me Cl H Me Cl Me Cl H OMe CF₃ Me Cl H Me SCF₃ Me Cl H 2-BrPh CF₃ Me Cl H Me I Me Cl H 2-MePh CF₃ Me Cl H Me SMe Me Cl H 2-CNPh CF₃ Me Cl H Me OMe Me Cl H 2-FPh CF₃ Me Cl H Me OEt Me Cl H 2,6-F₂Ph CF₃ Me Cl H Me Et Me Cl H 2,4-F₂Ph CF₃ Me Cl H Me SO₂Me Me Cl H 2,5-F₂Ph CF₃ Me Cl H Me SO₂CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H Et CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H Et Br Me Cl H 3-CF₃₋₂₋ CF₃ pyridyl Me Cl H Et Cl Me Cl H 3-Me-2- CF₃ pyridyl Me Cl H Ph CF₃ Et Cl H H OCF₃ Me Cl H Ph Br Et Cl H H C₂F₅ Me Cl H Ph Cl Et Cl H Me CF₃ Me Cl H 2-pyridyl CF₃ Et Cl H Me C₂F₅ Me Cl H 2-pyridyl Cl i-Pr Cl H Me CF₃

TABLE 9

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H H H CF₃ Me H Me H OCF₃ Me H H H OCF₃ Me H Me Me CF₃ Me H H Me CF₃ Me H Me Me OCF₃ Me H H Me OCF₃ Me H Me Me OCHF₂ Me H H Me OCHF₂ Me H Me Me C₂F₅ Me H H Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H H Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Br Me H H Me Br Me H Me Me Cl Me H H Me Cl Me H Me Me SCF₃ Me H H Me SCF₃ Me H Me Me I Me H H Me I Me H Me Me SMe Me H H Me SMe Me H Me Me OMe Me H H Me OMe Me H Me Me OEt Me H H Me OEt Me H Me Me Et Me H H Me Et Me H Me Me SO₂Me Me H H Me SO₂Me Me H Me Me SO₂CF₃ Me H H Me SO₂CF₃ Me H Me Et CF₃ Me H H Et CF₃ Me H Me Et Br Me H H Et Br Me H Me Et Cl Me H H Et Cl Me H Me Ph CF₃ Me H H Ph CF₃ Me H Me Ph Br Me H H Ph Br Me H Me Ph Cl Me H H Ph Cl Me H Me 2-pyridyl CF₃ Me H H 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H H 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H H 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H H 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H H 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H H 2-ClPh Br Me H Me 2-ClPh Cl Me H H 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Br Me H Me 3-C1-2-pyridyl Cl Me H H 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H H 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H H CF₃ Me Me H Me n-Pr CF₃ Me H H n-Pr CF₃ Me H Me i-Pr CF₃ Me H H i-Pr CF₃ Me H Me CF₃ CF₃ Me H H CF₃ CF₃ Me H Me OMe CF₃ Me H H OMe CF₃ Me H Me 2-BrPh CF₃ Me H H 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H H 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H H 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H H 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2- CF₃ Me H H 3-CF₃-2- CF₃ pyridyl pyridyl Me H Me 3-Me-2- CF₃ Me H H 3-Me-2- CF₃ pyridyl pyridyl Et H Me Me CF₃ Et H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ Et H Me Me OCF₃ Et H H Me OCF₃ Me Me H Me C₂F₅ i-Pr H H Me C₂F₅ Me Me H Me OCF₂CHF₂ i-Pr H H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ i-Pr H H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ i-Pr H H Me n-C₃F₇ Me Me H Me i-C₃F₇ i-Pr H H Me i-C₃F₇ Me Me H Me Br i-Pr H H Me Br Me Me H Me Cl i-Pr H H Me Cl Me Me H Me SCF₃ i-Pr H H Me SCF₃ Me Me H Me I i-Pr H H Me I Me Me H Me SMe i-Pr H H Me SMe Me Me H Me OMe i-Pr H H Me OMe Me Me H Me OEt i-Pr H H Me OEt Me Me H Me Et i-Pr H H Me Et Me Me H Me SO₂Me i-Pr H H Me SO₂Me Me Me H Me SO₂CF₃ i-Pr H H Me SO₂CF₃ Me Me H Et CF₃ i-Pr H H Et CF₃ Me Me H Et Br i-Pr H H Et Br Me Me H Et Cl i-Pr H H Et Cl Me Me H Ph CF₃ i-Pr H H Ph CF₃ Me Me H Ph Br i-Pr H H Ph Br Me Me H Ph Cl i-Pr H H Ph Cl Me Me H 2-pyridyl CF₃ i-Pr H H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl i-Pr H H 2-pyridyl Cl Me Me H 2-ClPh CF₃ i-Pr H H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ i-Pr H H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ i-Pr H H 2-ClPh SCHF₂ Me Me H 2-ClPh Br i-Pr H H 2-ClPh Br Me Me H 2-ClPh Cl i-Pr H H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ i-Pr H H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ i-Pr H H 3-C1-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ i-Pr H H 3-C1-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br i-Pr H H 3-C1-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl i-Pr H H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ i-Pr H H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ i-Pr H H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br i-Pr H H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl i-Pr H H 3-Br-2-pyridyl Cl Me Me H CF₃ Me i-Pr H H CF₃ Me Me Me H n-Pr CF₃ i-Pr H H n-Pr CF₃ Me Me H i-Pr CF₃ i-Pr H H i-Pr CF₃ Me Me H CF₃ CF₃ i-Pr H H CF₃ CF₃ Me Me H 2-BrPh CF₃ i-Pr H H 2-BrPh CF₃ Me Me H 2-MePh CF₃ i-Pr H H 2-MePh CF₃ Me Me H 2-CNPh CF₃ i-Pr H H 2-CNPh CF₃ Me Me H 2-FPh CF₃ i-Pr H H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ i-Pr H H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ i-Pr H H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ i-Pr H H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ i-Pr H H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ i-Pr H H 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2- CF₃ i-Pr H H 3-CF₃-2- CF₃ pyridyl pyridyl Me Me H 3-Me-2- CF₃ i-Pr H H 3-Me-2- CF₃ pyridyl pyridyl Et Me H Me CF₃ i-Pr Me H Me CF₃ Et Me H Me C₂F₅ i-Pr Me H Me C₂F₅ Et Me H Me OCF₃ i-Pr Me H Me OCF₃ Me Cl H Me CF₃ Me Cl H 2-ClPh Br Me Cl H Me OCF₃ Me Cl H 2-ClPh Cl Me Cl H Me OCHF₂ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H Me C₂F₅ Me Cl H 3-C1-2-pyridyl OCF₃ Me Cl H Me OCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H Me SCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl Br Me Cl H Me n-C₃F₇ Me Cl H 3-C1-2-pyridyl Cl Me Cl H Me i-C₃F₇ Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H Me Br Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H Me Cl Me Cl H 3-Br-2-pyridyl Br Me Cl H Me SCF₃ Me Cl H 3-Br-2-pyridyl Cl Me Cl H Me I Me Cl H CF₃ Me Me Cl H Me SMe Me Cl H n-Pr CF₃ Me Cl H Me OMe Me Cl H i-Pr CF₃ Me Cl H Me OEt Me Cl H CF₃ CF₃ Me Cl H Me Et Me Cl H 2-BrPh CF₃ Me Cl H Me SO₂Me Me Cl H 2-MePh CF₃ Me Cl H Me SO₂CF₃ Me Cl H 2-CNPh CF₃ Me Cl H Et CF₃ Me Cl H 2-FPh CF₃ Me Cl H Et Br Me Cl H 2,6-F₂Ph CF₃ Me Cl H Et Cl Me Cl H 2,4-F₂Ph CF₃ Me Cl H Ph CF₃ Me Cl H 2,5-F₂Ph CF₃ Me Cl H Ph Br Me Cl H 2-MeOPh CF₃ Me Cl H Ph Cl Me Cl H 3-F-2-pyridyl CF₃ Me Cl H 2-pyridyl CF₃ Me Cl H 3-CF₃-2- CF₃ pyridyl Me Cl H 2-pyridyl Cl Me Cl H 3-Me-2- CF₃ pyridyl Me Cl H 2-ClPh CF₃ Et Cl H Me CF₃ Me Cl H 2-ClPh OCF₃ Et Cl H Me C₂F₅ Me Cl H 2-ClPh SCHF₂ i-Pr Cl H Me CF₃

TABLE 10

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CHF₂ Me H H H CHF₂ Me H Me H CH₂CF₃ Me H H H CH₂CF₃ Et H Me H CH₂CF₃ Et H H H CH₂CF₃ Me H Me Me CH₂CF₃ Me H H Me CH₂CF₃ Me H Me Et CH₂CF₃ Me H H Et CH₂CF₃ Me H Me Me CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me Et CHF₂ Me H H Et CHF₂ Me H Me Me CHF₂ Me H H Me CHF₂ Me H Me Me CBrF₂ Me H H Me CBrF₂ Me H Me Me CHF₂ Me H H Me CHF₂ Et H Me Me CH₂CF₃ Et H H Me CH₂CF₃ Me H Me Me Et Me H H Me Et Me H Me Me n-Pr Me H H Me n-Pr Me H Me Me CH₂C₂F₅ Me H H Me CH₂C₂F₅ n-Pr H Me Me CH₂CF₃ n-Pr H H Me CH₂CF₃ Me H Me Me CF₃ Me H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ Me H Me Et CHF₂ Me H H Et CHF₂ Me H Me n-Pr CH₂CF₃ Me H H n-Pr CH₂CF₃ Me H Me i-Pr CHF₂ Me H H i-Pr CHF₂ Me H Me Cl CH₂CF₃ Me H H Cl CH₂CF₃ Me H Me F CH₂CF₃ Me H H F CH₂CF₃ Me H Me Me CH₂Cl Me H H Me CH₂Cl Me H Me Me CClF₂ Me H H Me CClF₂ Me H Me Me CH₂CH₂Cl Me H H Me CH₂CH₂Cl Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Allyl Me H H Me Allyl Me H Me Et CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me Et i-C₃F₇ Me H H Me i-C₃F₇ Me H Me i-Pr CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me n-Pr CF₂CHF₂ Me H H Me CF₂CHF₂ Me H Me CF₃ CF₂CHF₂ Me H H CF₃ CF₂CHF₂ Me H Me CF₃ Me Me H H CF₃ Me Me H Me OMe CH₂CF₃ Me H H OMe CH₂CF₃ Me H Me H CH₂CF₃ Me H H H CH₂CF₃ Me H Me H CH₂CF₃ Me H H H CH₂CF₃ Me H Me H C₂F₅ Me H H H C₂F₅ Et H Me H C₂F₅ Et H H H C₂F₅ Me H Me H C₂F₅ Me H H H C₂F₅ Me H Me H CF₂CHF₂ Me H H H CF₂CHF₂ Me H Me i-Pr CH₂CF₃ Me H H H CH₂CF₃ Me H Me H n-C₃F₇ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H H H i-C₃F₇ Me H Me Ph CH₂CF₃ Me H H H CH₂CF₃ Me H Me Ph CF₂CHF₂ Me H H H CF₂CHF₂ Me H Me Ph CHF₂ Me H H H CHF₂ Me H Me 2-pyridyl CH₂CF₃ Me H H Ph CH₂CF₃ Me H Me 2-pyridyl CF₂CHF₂ Me H H Ph CF₂CHF₂ Me H Me 2-ClPh CH₂CF₃ Me H H Ph CH₂CF₃ Me H Me 2-ClPh CF₂CHF₂ Me H H 2-pyridyl CF₂CHF₂ Me H Me 2-ClPh CHF₂ Me H H 2-pyridyl CHF₂ Me H Me 2-ClPh Et Me H H 2-ClPh Et Me H Me 2-ClPh CBrF₂ Me H H 2-ClPh CBrF₂ Me H Me 2-BrPh CH₂CF₃ Me H H 2-ClPh CH₂CF₃ Me H Me 2-MePh CH₂CF₃ Me H H 2-ClPh CH₂CF₃ Me H Me 2-CNPh CH₂CF₃ Me H H 2-ClPh CH₂CF₃ Me H Me 2-FPh CH₂CF₃ Me H H 2-BrPh CH₂CF₃ Me H Me 2,6-F₂Ph CH₂CF₃ Me H H 2-MePh CH₂CF₃ Me H Me 2,4-F₂Ph CH₂CF₃ Me H H 2-CNPh CH₂CF₃ Me H Me 2,5-F₂Ph CH₂CF₃ Me H H 2-EPh CH₂CF₃ Me H Me 2-MeOPh CH₂CF₃ Me H H 2,6-F₂Ph CH₂CF₃ Me H Me 3-Cl-2-pyridyl CH₂CF₃ Me H H 2,4-F₂Ph CH₂CF₃ Me H Me 3-Cl-2-pyridyl CF₂CHF₂ Me H H 2,5-F₂Ph CF₂CHF₂ Me H Me 3-Cl-2-pyridyl CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-C1-2-pyridyl CHF₂ Me H H 3-Cl-2-pyridyl CHF₂ Me H Me 3-Cl-2-pyridyl CBrF₂ Me H H 3-Cl-2-pyridyl CBrF₂ Me H Me 3-F-2-pyridyl CH₂CF₃ Me H H 3-Cl-2-pyridyl CH₂CF₃ Me H Me 3-CF₃-2- CH₂CF₃ Me H H 3-CF₃-2- CH₂CF₃ pyridyl pyridyl Me H Me 3-Me-2- CH₂CF₃ Me H H 3-Me-2- CF₂CHF₂ pyridyl pyridyl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-Br-2-pyndyl CH₂CF₃ Me H H 3-Cl-2-pyridyl CH₂CF₃ Me H Me 3-Br-2-pyridyl CF₂CHF₂ Me H H 3-Cl-2-pyridyl CH₂CF₃ Me H Me 3-Br-2-pyridyl CClF₂ Me H H 3-Br-2-pyridyl CClF₂ Me Me H H CHF₂ Me H H 3-Br-2-pyridyl CH₂CF₃ Me Me H H CH₂CF₃ Me H H 3-Br-2-pyridyl CF₃ Et Me H H CH₂CF₃ Me H H 3-Br-2-pyridyl CF₃ Me Me H Me CH₂CF₃ i-Pr H H Et CH₂C₂F₅ Me Me H Et CH₂CF₃ i-Pr H H n-Pr CH₂CF₃ Me Me H Me CF₂CHF₂ i-Pr H H i-Pr CF₃ Me Me H Et CHF₂ i-Pr H H Cl C₂F₅ Me Me H Me CHF₂ i-Pr H H F CHF₂ Me Me H Me CBrF₂ i-Pr H H Me CH₂CF₃ Me Me H Me CHF₂ i-Pr H H Me CHF₂ Et Me H Me CH₂CF₃ i-Pr H H Me CH₂CF₃ Me Me H Me Et i-Pr H H Me CH₂CF₃ Me Me H Me n-Pr i-Pr H H Me CH₂Cl Me Me H Me CH₂C₂F₅ i-Pr H H Me CClF₂ n-Pr Me H Me CH₂CF₃ i-Pr H H Me CH₂CH₂Cl Me Me H Me CF₃ i-Pr H H Me n-C₃F₇ Et Me H Me C₂F₅ i-Pr H H Me i-C₃F₇ Me Me H Et CHF₂ i-Pr H H Me Allyl Me Me H n-Pr CH₂CF₃ i-Pr H H CF₃ CF₂CHF₂ Me Me H i-Pr CHF₂ i-Pr H H CF₃ i-C₃F₇ Me Me H Cl CH₂CF₃ i-Pr H H OMe CF₂CHF₂ Me Me H F CH₂CF₃ i-Pr H H H CF₂CHF₂ Me Me H Me CH₂Cl i-Pr H H H CF₂CHF₂ Me Me H Me CClF₂ i-Pr H H H Me Me Me H Me CH₂CH₂Cl i-Pr H H H CH₂CF₃ Me Me H Me n-C₃F₇ i-Pr H H H CH₂CF₃ Me Me H Me i-C₃F₇ i-Pr H H H C₂F₅ Me Me H Me Allyl i-Pr H H H C₂F₅ Me Me H Me CF₂CHF₂ i-Pr H H H C₂F₅ Me Me H Me i-C₃F₇ i-Pr H H H CF₂CHF₂ Me Me H Me CF₂CHF₂ i-Pr H H H CH₂CF₃ Me Me H Me CF₂CHF₂ i-Pr H H H n-C₃F₇ Me Me H CF₃ CF₂CHF₂ i-Pr H H Ph i-C₃F₇ Me Me H CF₃ Me i-Pr H H Ph CH₂CF₃ Me Me H OMe CH₂CF₃ i-Pr H H Ph CF₂CHF₂ Me Me H H CH₂CF₃ i-Pr H H 2-pyiidyl CHF₂ Me Me H H CH₂CF₃ i-Pr H H 2-pyridyl CH₂CF₃ Me Me H H C₂F₅ i-Pr H H 2-ClPh CF₂CHF₂ Et Me H H C₂F₅ i-Pr H H 2-ClPh CH₂CF₃ Me Me H H C₂F₅ i-Pr H H 2-ClPh CF₂CHF₂ Me Me H H CF₂CHF₂ i-Pr H H 2-ClPh CHF₂ Me Me H H CH₂CF₃ i-Pr H H 2-ClPh Et Me Me H H n-C₃F₇ i-Pr H H 2-BrPh CBrF₂ Me Me H H i-C₃F₇ i-Pr H H 2-MePh CH₂CF₃ Me Me H H CH₂CF₃ i-Pr H H 2-CNPh CH₂CF₃ Me Me H H CF₂CHF₂ i-Pr H H 2-FPh CH₂CF₃ Me Me H H CHF₂ i-Pr H H 2,6-F₂Ph CH₂CF₃ Me Me H Ph CH₂CF₃ i-Pr H H 2,4-F₂Ph CH₂CF₃ Me Me H Ph CF₂CHF₂ i-Pr H H 2,5-F₂Ph CH₂CF₃ Me Me H Ph CH₂CF₃ i-Pr H H 2-MeOPh CH₂CF₃ Me Me H 2-pyridyl CF₂CHF₂ i-Pr H H 3-Cl-2-pyridyl CH₂CF₃ Me Me H 2-pyridyl CHF₂ i-Pr H H 3-Cl-2-pyridyl CH₂CF₃ Me Me H 2-ClPh Et i-Pr H H 3-Cl-2-pyridyl CF₂CHF₂ Me Me H 2-ClPh CBrF₂ i-Pr H H 3-Cl-2-pyridyl CF₃ Me Me H 2-ClPh CH₂CF₃ i-Pr H H 3-Cl-2-pyridyl CHF₂ Me Me H 2-ClPh CH₂CF₃ i-Pr H H 3-F-2-pyridyl CBrF₂ Me Me H 2-ClPh CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CH₂CF₃ Me Me H 2-BrPh CH₂CF₃ i-Pr H H 3-CF₃-2- CH₂CF₃ pyridyl Me Me H 2-MePh CH₂CF₃ i-Pr H H 3-Me-2- CH₂CF₃ pyridyl Me Me H 2-CNPh CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CF₃ Me Me H 2-FPh CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CH₂CF₃ Me Me H 2,6-F₂Ph CH₂CF₃ i-Pr H H 3-Br-2-pyridyl CF₂CHF₂ Me Me H 2,4-F₂Ph CH₂CF₃ Me Cl H F CH₂CF₃ Me Me H 2,5-F₂Ph CF₂CHF₂ Me Cl H Me CHF₂ Me Me H 2-MeOPh CF₃ Me Cl H Me CH₂CF₃ Me Me H 3-Cl-2-pyridyl CHF₂ Me Cl H Me CH₂CF₃ Me Me H 3-Cl-2-pyridyl CBrF₂ Me Cl H Me CH₂Cl Me Me H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H Me CClF₂ Me Me H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H Me CH₂CH₂Cl Me Me H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H Me n-C₃F₇ Me Me H 3-F-2-pyridyl CF₃ Me Cl H Me i-C₃F₇ Me Me H 3-CF₃-2- CH₂CF₃ Me Cl H Me Allyl pyridyl Me Me H 3-Me-2- CF₂CHF₂ Me Cl H Me CF₂CHF₂ pyridyl Me Me H 3-Br-2-pyridyl CClF₂ Me Cl H CF₃ i-C₃F₇ Me Me H 3-Br-2-pyridyl CH₂CF₃ Me Cl H CF₃ CF₂CHF₂ Me Me H 3-Br-2-pyridyl CF₃ Me Cl H OMe CF₂CHF₂ Me Me H 3-Br-2-pyridyl CF₃ Me Cl H H CF₂CHF₂ Me Cl H Me CHF₂ Me Cl H H Me Me Cl H Et CH₂CF₃ Me Cl H H CH₂CF₃ Me Cl H Me CH₂CF₃ Et Cl H H CH₂CF₃ Me Cl H Et CH₂CF₃ Me Cl H H CH₂CF₃ Me Cl H Me CH₂CF₃ Me Cl H H C₂F₅ Me Cl H Me CF₂CHF₂ Me Cl H H C₂F₅ Me Cl H Me CHF₂ Me Cl H H C₂F₅ Et Cl H Me CHF₂ Me Cl H H CF₂CHF₂ Me Cl H Me CBrF₂ Me Cl H H CH₂CF₃ Me Cl H Me CHF₂ Me Cl H H n-C₃F₇ Me Cl H Me CH₂CF₃ Me Cl H 3-Me-2- CH₂CF₃ pyridyl n-Pr Cl H Me Et Me Cl H H i-C₃F₇ Me Cl H Me n-Pr Me Cl H Ph CH₂CF₃ Et Cl H Me CH₂C₂F₅ Me Cl H Ph CF₂CHF₂ Me Cl H Et CH₂CF₃ Me Cl H Ph CHF₂ Me Cl H n-Pr CF₃ Me Cl H 2-pyridyl CH₂CF₃ Me Cl H i-Pr C₂F₅ Me Cl H 2-pyridyl CF₂CHF₂ Me Cl H Cl CHF₂ Me Cl H 2-ClPh CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CH₂CF₃ Me Cl H 2-ClPh CF₂CHF₂ Me Cl H 3-Cl-2-pyridyl CF₂CHF₂ Me Cl H 2-FPh CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H 2,6-F₂Ph CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CHF₂ Me Cl H 2,4-F₂Ph CH₂CF₃ Me Cl H 3-Cl-2-pyridyl CBrF₂ Me Cl H 2-ClPh Et Me Cl H 3-F-2-pyridyl CH₂CF₃ Me Cl H 2-ClPh CBrF₂ Me Cl H 3-CF₃-2- CH₂CF₃ Me Cl H 2-BrPh CH₂CF₃ pyridyl Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H 2-MePh CH₂CF₃ Me Cl H 3-Br-2-pyridyl CH₂CF₃ Me Cl H 2-CNPh CH₂CF₃ Me Cl H 3-Br-2-pyiidyl CF₂CHF₂ Me Cl H 2-MeOPh CH₂CF₃ Me Cl H 3-Br-2-pyridyl CClF₂ Me Cl H 2,5-F₂Ph CH₂CF₃ Me Cl H 2-ClPh CHF₂

TABLE 11

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H H H CF₃ Me H Me H OCF₃ Me H H H OCF₃ Me H Me H OCHF₂ Me H H H OCHF₂ Me H Me H C₂F₅ Me H H H C₂F₅ Me H Me H OCF₂CHF₂ Me H H H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H H H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H H H i-C₃F₇ Me H Me H Br Me H H H Br Me H Me H Cl Me H H H Cl Me H Me H SCF₃ Me H H H SCF₃ Me H Me Me CF₃ Me H H Me CF₃ Me H Me Me OCF₃ Me H H Me OCF₃ Me H Me Me OCHF₂ Me H H Me OCHF₂ Me H Me Me C₂F₅ Me H H Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H H Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Br Me H H Me Br Me H Me Me Cl Me H H Me Cl Me H Me Me SCF₃ Me H H Me SCF₃ Me H Me Me I Me H H Me I Me H Me Me SMe Me H H Me SMe Me H Me Me OMe Me H H Me OMe Me H Me Me OEt Me H H Me OEt Me H Me Me Et Me H H Me Et Me H Me Me SO₂Me Me H H Me SO₂Me Me H Me Me SO₂CF₃ Me H H Me SO₂CF₃ Me H Me Et CF₃ Me H H Et CF₃ Me H Me Et Br Me H H Et Br Me H Me Et Cl Me H H Et Cl Me H Me Ph CF₃ Me H H Ph CF₃ Me H Me Ph Br Me H H Ph Br Me H Me Ph Cl Me H H Ph Cl Me H Me 2-pyridyl CF₃ Me H H 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H H 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H H 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H H 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H H 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H H 2-ClPh Br Me H Me 2-ClPh Cl Me H H 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H H 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H H 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H H CF₃ Me Me H Me F CF₃ Me H H F CF₃ Me H Me Cl CF₃ Me H H Cl CF₃ Me H Me n-Pr CF₃ Me H H n-Pr CF₃ Me H Me i-Pr CF₃ Me H H i-Pr CF₃ Me H Me CF₃ CF₃ Me H H CF₃ CF₃ Me H Me OMe CF₃ Me H H OMe CF₃ Me H Me 2-BrPh CF₃ Me H H 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H H 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H H 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H H 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2- CF₃ Me H H 3-CF₃-2- CF₃ pyridyl pyridyl Me H Me 3-Me-2- CF₃ Me H H 3-Me-2- CF₃ pyridyl pyridyl Et H Me H OCF₃ Et H H H OCF₃ Et H Me H C₂F₅ Et H H H C₂F₅ Et H Me Me CF₃ Et H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ i-Pr H Me Me CF₃ i-Pr H H Me CF₃ Me Me H H CF₃ Me H Cl H CF₃ Me Me H H OCF₃ Me H Cl H OCF₃ Me Me H H OCHF₂ Me H Cl H OCHF₂ Me Me H H C₂F₅ Me H Cl H C₂F₅ Me Me H H OCF₂CHF₂ Me H Cl H OCF₂CHF₂ Me Me H H SCF₂CHF₂ Me H Cl H SCF₂CHF₂ Me Me H H n-C₃F₇ Me H Cl H n-C₃F₇ Me Me H H i-C₃F₇ Me H Cl H i-C₃F₇ Me Me H H Br Me H Cl H Br Me Me H H Cl Me H Cl H Cl Me Me H H SCF₃ Me H Cl H SCF₃ Me Me H H CF₃ Me H Cl Me CF₃ Me Me H H OCF₃ Me H Cl Me OCF₃ Me Me H H OCHF₂ Me H Cl Me OCHF₂ Me Me H Me C₂F₅ Me H Cl Me C₂F₅ Me Me H Me OCF₂CHF₂ Me H Cl Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ Me H Cl Me SCF₂CHIF2 Me Me H Me n-C₃F₇ Me H Cl Me n-C₃F₇ Me Me H Me i-C₃F₇ Me H Cl Me i-C₃F₇ Me Me H Me Br Me H Cl Me Br Me Me H Me Cl Me H Cl Me Cl Me Me H Me SCF₃ Me H Cl Me SCF₃ Me Me H Me I Me H Cl Me I Me Me H Me SMe Me H Cl Me SMe Me Me H Me OMe Me H Cl Me OMe Me Me H Me OEt Me H Cl Me OEt Me Me H Me Et Me H Cl Me Et Me Me H Me SO₂Me Me H Cl Me SO₂Me Me Me H Me SO₂CF₃ Me H Cl Me SO₂CF₃ Me Me H Et CF₃ Me H Cl Et CF₃ Me Me H Et Br Me H Cl Et Br Me Me H Et Cl Me H Cl Et Cl Me Me H Ph CF₃ Me H Cl Ph CF₃ Me Me H Ph Br Me H Cl Ph Br Me Me H Ph Cl Me H Cl Ph Cl Me Me H 2-pyridyl CF₃ Me H Cl 2-pyridyl CF₃ Me Me H 2-pyridyl Cl Me H Cl 2-pyridyl Cl Me Me H 2-ClPh CF₃ Me H Cl 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ Me H Cl 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ Me H Cl 2-ClPh SCHF₂ Me Me H 2-ClPh Br Me H Cl 2-ClPh Br Me Me H 2-ClPh Cl Me H Cl 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ Me H Cl 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ Me H Cl 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ Me H Cl 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br Me H Cl 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl Me H Cl 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ Me H Cl 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ Me H Cl 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br Me H Cl 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl Me H Cl 3-Br-2-pyridyl Cl Me Me H CF₃ Me Me H Cl CF₃ Me Me Me H F CF₃ Me H Cl F CF₃ Me Me H Cl CF₃ Me H Cl Cl CF₃ Me Me H n-Pr CF₃ Me H Cl n-Pr CF₃ Me Me H i-Pr CF₃ Me H Cl i-Pr CF₃ Me Me H CF₃ CF₃ Me H Cl CF₃ CF₃ Me Me H OMe CF₃ Me H Cl OMe CF₃ Me Me H 2-BrPh CF₃ Me H Cl 2-BrPh CF₃ Me Me H 2-MePh CF₃ Me H Cl 2-MePh CF₃ Me Me H 2-CNPh CF₃ Me H Cl 2-CNPh CF₃ Me Me H 2-FPh CF₃ Me H Cl 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ Me H Cl 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ Me H Cl 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ Me H Cl 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ Me H Cl 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ Me H Cl 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2- CF₃ Me H Cl 3-CF₃-2- CF₃ pyridyl pyridyl Me Me H 3-Me-2- CF₃ Me H Cl 3-Me-2- CF₃ pyridyl pyridyl Et Me H H OCF₃ Et H Cl H OCF₃ Et Me H H C₂F₅ Et H Cl H C₂F₅ Et Me H Me CF₃ Et H Cl Me CF₃ Et Me H Me C₂F₅ Et H Cl Me C₂F₅ i-Pr Me H Me CF₃ i-Pr H Cl Me CF₃ Me Cl H H CF₃ Me Cl H 2-ClPh CF₃ Me Cl H H OCF₃ Me Cl H 2-ClPh OCF₃ Me Cl H H OCHF₂ Me Cl H 2-ClPh SCHF₂ Me Cl H H C₂F₅ Me Cl H 2-ClPh Br Me Cl H H OCF₂CHF₂ Me Cl H 2-ClPh Cl Me Cl H H SCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H H n-C₃F₇ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H H i-C₃F₇ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H H Br Me Cl H 3-Cl-2-pyridyl Br Me Cl H H Cl Me Cl H 3-Cl-2-pyridyl Cl Me Cl H H SCF₃ Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H Me CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H Me OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H Me OCHF₂ Me Cl H 3-Br-2-pyridyl Cl Me Cl H Me C₂F₅ Me Cl H CF₃ Me Me Cl H Me OCF₂CHF₂ Me Cl H F CF₃ Me Cl H Me SCF₂CHF₂ Me Cl H Cl CF₃ Me Cl H Me n-C₃F₇ Me Cl H n-Pr CF₃ Me Cl H Me i-C₃F₇ Me Cl H i-Pr CF₃ Me Cl H Me Br Me Cl H CF₃ CF₃ Me Cl H Me Cl Me Cl H OMe CF₃ Me Cl H Me SCF₃ Me Cl H 2-BrPh CF₃ Me Cl H Me I Me Cl H 2-MePh CF₃ Me Cl H Me SMe Me Cl H 2-CNPh CF₃ Me Cl H Me OMe Me Cl H 2-FPh CF₃ Me Cl H Me OEt Me Cl H 2,6-F₂Ph CF₃ Me Cl H Me Et Me Cl H 2,4-F₂Ph CF₃ Me Cl H Me SO₂Me Me Cl H 2,5-F₂Ph CF₃ Me Cl H Me SO₂CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H Et CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H Et Br Me Cl H 3-CF₃-2- CF₃ pyridyl Me Cl H Et Cl Me Cl H 3-Me-2- CF₃ pyridyl Me Cl H Ph CF₃ Et Cl H H OCF₃ Me Cl H Ph Br Et Cl H H C₂F₅ Me Cl H Ph Cl Et Cl H Me CF₃ Me Cl H 2-pyridyl CF₃ Et Cl H Me C₂F₅ Me Cl H 2-pyridyl Cl i-Pr Cl H Me CF₃

TABLE 12

R³ R^(4a) R⁶ R^(5a) R^(5b) R³ R^(4a) R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H H H CF₃ Me H Me H OCF₃ Me H H H OCF₃ Me H Me H OCHF₂ Me H H H OCHF₂ Me H Me H C₂F₅ Me H H H C₂F₅ Me H Me H OCF₂CHF₂ Me H H H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H H H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H H H n-C₃F₇ Me H Me H i-C₃F₇ Me H H H i-C₃F₇ Me H Me H Br Me H H H Br Me H Me H Cl Me H H H Cl Me H Me H SCF₃ Me H H H SCF₃ Me H Me Me CF₃ Me H H Me CF₃ Me H Me Me OCF₃ Me H H Me OCF₃ Me H Me Me OCHF₂ Me H H Me OCHF₂ Me H Me Me C₂F₅ Me H H Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H H Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H H Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H H Me i-C₃F₇ Me H Me Me Br Me H H Me Br Me H Me Me Cl Me H H Me Cl Me H Me Me SCF₃ Me H H Me SCF₃ Me H Me Me I Me H H Me I Me H Me Me SMe Me H H Me SMe Me H Me Me OMe Me H H Me OMe Me H Me Me OEt Me H H Me OEt Me H Me Me Et Me H H Me Et Me H Me Me SO₂Me Me H H Me SO₂Me Me H Me Me SO₂CF₃ Me H H Me SO₂CF₃ Me H Me Et CF₃ Me H H Et CF₃ Me H Me Et Br Me H H Et Br Me H Me Et Cl Me H H Et Cl Me H Me Ph CF₃ Me H H Ph CF₃ Me H Me Ph Br Me H H Ph Br Me H Me Ph Cl Me H H Ph Cl Me H Me 2-pyridyl CF₃ Me H H 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H H 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H H 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H H 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H H 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H H 2-ClPh Br Me H Me 2-ClPh Cl Me H H 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H H 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H H 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H H CF₃ Me Me H Me F CF₃ Me H H F CF₃ Me H Me Cl CF₃ Me H H Cl CF₃ Me H Me n-Pr CF₃ Me H H n-Pr CF₃ Me H Me i-Pr CF₃ Me H H i-Pr CF₃ Me H Me CF₃ CF₃ Me H H CF₃ CF₃ Me H Me OMe CF₃ Me H H OMe CF₃ Me H Me 2-BrPh CF₃ Me H H 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H H 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H H 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H H 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H H 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H H 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H H 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2- CF₃ Me H H 3-CF₃-2- CF₃ pyridyl pyridyl Me H Me 3-Me-2- CF₃ Me H H 3-Me-2- CF₃ pyridyl pyridyl Et H Me H OCF₃ Et H H H OCF₃ Et H Me H C₂F₅ Et H H H C₂F₅ Et H Me Me CF₃ Et H H Me CF₃ Et H Me Me C₂F₅ Et H H Me C₂F₅ i-Pr H Me Me CF₃ i-Pr H H Me CF₃ Me Me H H CF₃ Me H Cl H CF₃ Me Me H H OCF₃ Me H Cl H OCF₃ Me Me H H OCHF₂ Me H Cl H OCHF₂ Me Me H H C₂F₅ Me H Cl H C₂F₅ Me Me H H OCF₂CHF₂ Me H Cl H OCF₂CHF₂ Me Me H H SCF₂CHF₂ Me H Cl H SCF₂CHF₂ Me Me H H n-C₃F₇ Me H Cl H n-C₃F₇ Me Me H H i-C₃F₇ Me H Cl H i-C₃F₇ Me Me H H Br Me H Cl H Br Me Me H H Cl Me H Cl H Cl Me Me H H SCF₃ Me H Cl H SCF₃ Me Me H H CF₃ Me H Cl Me CF₃ Me Me H H OCF₃ Me H Cl Me OCF₃ Me Me H H OCHF₂ Me H Cl Me OCHF₂ Me Me H Me C₂F₅ Me H Cl Me C₂F₅ Me Me H Me OCF₂CHF₂ Me H Cl Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ Me H Cl Me SCF₂CHF₂ Me Me H Me n-C₃F₇ Me H Cl Me n-C₃F₇ Me Me H Me i-C₃F₇ Me H Cl Me i-C₃F₇ Me Me H Me Br Me H Cl Me Br Me Me H Me Cl Me H Cl Me Cl Me Me H Me SCF₃ Me H Cl Me SCF₃ Me Me H Me I Me H Cl Me I Me Me H Me SMe Me H Cl Me SMe Me Me H Me OMe Me H Cl Me OMe Me Me H Me OEt Me H Cl Me OEt Me Me H Me Et Me H Cl Me Et Me Me H Me SO₂Me Me H Cl Me SO₂Me Me Me H Me SO₂CF₃ Me H Cl Me SO₂CF₃ Me Me H Et CF₃ Me H Cl Et CF₃ Me Me H Et Br Me H Cl Et Br Me Me H Et Cl Me H Cl Et Cl Me Me H Ph CF₃ Me H Cl Ph CF₃ Me Me H Ph Br Me H Cl Ph Br Me Me H Ph Cl Me H Cl Ph Cl Me Me H 2-pyridyl CF₃ Me H Cl 2-pyridyl CF₃ Me Me H 2-pyridyl Cl Me H Cl 2-pyridyl Cl Me Me H 2-ClPh CF₃ Me H Cl 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ Me H Cl 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ Me H Cl 2-ClPh SCHF₂ Me Me H 2-ClPh Br Me H Cl 2-ClPh Br Me Me H 2-ClPh Cl Me H Cl 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ Me H Cl 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF₃ Me H Cl 3-Cl-2-pyridyl OCF₃ Me Me H 3-Cl-2-pyridyl SCHF₂ Me H Cl 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br Me H Cl 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl Me H Cl 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ Me H Cl 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ Me H Cl 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br Me H Cl 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl Me H Cl 3-Br-2-pyridyl Cl Me Me H CF₃ Me Me H Cl CF₃ Me Me Me H F CF₃ Me H Cl F CF₃ Me Me H Cl CF₃ Me H Cl Cl CF₃ Me Me H n-Pr CF₃ Me H Cl n-Pr CF₃ Me Me H i-Pr CF₃ Me H Cl i-Pr CF₃ Me Me H CF₃ CF₃ Me H Cl CF₃ CF₃ Me Me H OMe CF₃ Me H Cl OMe CF₃ Me Me H 2-BrPh CF₃ Me H Cl 2-BrPh CF₃ Me Me H 2-MePh CF₃ Me H Cl 2-MePh CF₃ Me Me H 2-CNPh CF₃ Me H Cl 2-CNFh CF₃ Me Me H 2-FPh CF₃ Me H Cl 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ Me H Cl 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ Me H Cl 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ Me H Cl 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ Me H Cl 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ Me H Cl 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2- CF₃ Me H Cl 3-CF₃-2- CF₃ pyridyl pyridyl Me Me H 3-Me-2- CF₃ Me H Cl 3-Me-2- CF₃ pyridyl pyridyl Et Me H H OCF₃ Et H Cl H OCF₃ Et Me H H C₂F₅ Et H Cl H C₂F₅ Et Me H Me CF₃ Et H Cl Me CF₃ Et Me H Me C₂F₅ Et H Cl Me C₂F₅ i-Pr Me H Me CF₃ i-Pr H Cl Me CF₃ Me Cl H H CF₃ Me Cl H 2-ClPh CF₃ Me Cl H H OCF₃ Me Cl H 2-ClPh OCF₃ Me Cl H H OCHF₂ Me Cl H 2-ClPh SCHF₂ Me Cl H H C₂F₅ Me Cl H 2-ClPh Br Me Cl H H OCF₂CHF₂ Me Cl H 2-ClPh Cl Me Cl H H SCF₂CHF₂ Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H H n-C₃F₇ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H H i-C₃F₇ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H H Br Me Cl H 3-Cl-2-pyridyl Br Me Cl H H Cl Me Cl H 3-Cl-2-pyridyl Cl Me Cl H H SCF₃ Me Cl H 3-Br-2-pyridyl CF₃ Me Cl H Me CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H Me OCF₃ Me Cl H 3-Br-2-pyrzdyl Br Me Cl H Me OCHF₂ Me Cl H 3-Br-2-pyridyl Cl Me Cl H Me C₂F₅ Me Cl H CF₃ Me Me Cl H Me OCF₂CHF₂ Me Cl H F CF₃ Me Cl H Me SCF₂CHF₂ Me Cl H Cl CF₃ Me Cl H Me n-C₃F₇ Me Cl H n-Pr CF₃ Me Cl H Me i-C₃F₇ Me Cl H i-Pr CF₃ Me Cl H Me Br Me Cl H CF₃ CF₃ Me Cl H Me Cl Me Cl H OMe CF₃ Me Cl H Me SCF₃ Me Cl H 2-BrPh CF₃ Me Cl H Me I Me Cl H 2-MePh CF₃ Me Cl H Me SMe Me Cl H 2-CNPh CF₃ Me Cl H Me OMe Me Cl H 2-FPh CF₃ Me Cl H Me OEt Me Cl H 2,6-F₂Ph CF₃ Me Cl H Me Et Me Cl H 2,4-F₂Ph CF₃ Me Cl H Me SO₂Me Me Cl H 2,S-F₂Ph CF₃ Me Cl H Me SO₂CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H Et CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H Et Br Me Cl H 3-CF₃-2- CF₃ pyridyl Me Cl H Et Cl Me Cl H 3-Me-2- CF₃ pyridyl Me Cl H Ph CF₃ Et Cl H H OCF₃ Me Cl H Ph Br Et Cl H H C₂F₅ Me Cl H Ph Cl Et Cl H Me CF₃ Me Cl H 2-pyridyl CF₃ Et Cl H Me C₂F₅ Me Cl H 2-pyridyl Cl i-Pr Cl H Me CF₃

TABLE 13

R³ R^(4a) R^(5a) R^(5b) R³ R^(4a) R^(5a) R^(5b) Me H H CF₃ Me H H CF₃ Me H H OCF₃ Me H H OCF₃ Me H H OCHF₂ Me H H OCHF₂ Me H H C₂F₅ Me H H C₂F₅ Me H H OCF₂CHF₂ Me H H OCF₂CHF₂ Me H H SCF₂CHF₂ Me H H SCF₂CHF₂ Me H H n-C₃F₇ Me H H n-C₃F₇ Me H H i-C₃F₇ Me H H i-C₃F₇ Me H H Br Me H H Br Me H H Cl Me H H Cl Me H H SCF₃ Me H H SCF₃ Me H Me CF₃ Me H Me CF₃ Me H Me OCF₃ Me H Me OCF₃ Me H Me OCHF₂ Me H Me OCHF₂ Me H Me C₂F₅ Me H Me C₂F₅ Me H Me OCF₂CHF₂ Me H Me OCF₂CHF₂ Me H Me SCF₂CHF₂ Me H Me SCF₂CHF₂ Me H Me n-C₃F₇ Me H Me n-C₃F₇ Me H Me i-C₃F₇ Me H Me i-C₃F₇ Me H Me Br Me H Me Br Me H Me Cl Me H Me Cl Me H Me SCF₃ Me H Me SCF₃ Me H Me I Me H Me I Me H Me SMe Me H Me SMe Me H Me OMe Me H Me OMe Me H Me OEt Me H Me OEt Me H Me Et Me H Me Et Me H Me SO₂Me Me H Me SO₂Me Me H Me SO₂CF₃ Me H Me SO₂CF₃ Me H Et CF₃ Me H Et CF₃ Me H Et Br Me H Et Br Me H Et Cl Me H Et Cl Me H Ph CF₃ Me H Ph CF₃ Me H Ph Br Me H Ph Br Me H Ph Cl Me H Ph Cl Me H 2-pyridyl CF₃ Me H 2-pyridyl CF₃ Me H 2-pyridyl Cl Me H 2-pyridyl Cl Me H 2-ClPh CF₃ Me H 2-ClPh CF₃ Me H 2-ClPh OCF₃ Me H 2-ClPh OCF₃ Me H 2-ClPh SCHF₂ Me H 2-ClPh SCHF₂ Me H 2-ClPh Br Me H 2-ClPh Br Me H 2-ClPh Cl Me H 2-ClPh Cl Me H 3-Cl-2-pyridyl CF₃ Me H 3-Cl-2-pyridyl CF₃ Me H 3-Cl-2-pyridyl OCF₃ Me H 3-Cl-2-pyridyl OCF₃ Me H 3-Cl-2-pyridyl SCHF₂ Me H 3-Cl-2-pyridyl SCHF₂ Me H 3-Cl-2-pyridyl Br Me H 3-Cl-2-pyridyl Br Me H 3-Cl-2-pyridyl Cl Me H 3-Cl-2-pyridyl Cl Me H 3-Br-2-pyridyl CF₃ Me H 3-Br-2-pyridyl CF₃ Me H 3-Br-2-pyridyl OCF₃ Me H 3-Br-2-pyridyl OCF₃ Me H 3-Br-2-pyridyl Br Me H 3-Br-2-pyridyl Br Me H 3-Br-2-pyridyl Cl Me H 3-Br-2-pyridyl Cl Me H CF₃ Me Me H CF₃ Me Me H F CF₃ Me H F CF₃ Me H Cl CF₃ Me H Cl CF₃ Me H n-Pr CF₃ Me H n-Pr CF₃ Me H i-Pr CF₃ Me H i-Pr CF₃ Me H CF₃ CF₃ Me H CF₃ CF₃ Me H OMe CF₃ Me H OMe CF₃ Me H 2-BrPh CF₃ Me H 2-BrPh CF₃ Me H 2-MePh CF₃ Me H 2-MePh CF₃ Me H 2-CNPh CF₃ Me H 2-CNPh CF₃ Me H 2-FPh CF₃ Me H 2-FPh CF₃ Me H 2,6-F₂Ph CF₃ Me H 2,6-F₂Ph CF₃ Me H 2,4-F₂Ph CF₃ Me H 2,4-F₂Ph CF₃ Me H 2,5-F₂Ph CF₃ Me H 2,5-F₂Ph CF₃ Me H 2-MeOPh CF₃ Me H 2-MeOPh CF₃ Me H 3-F-2-pyridyl CF₃ Me H 3-F-2-pyridyl CF₃ Me H 3-CF₃₋₂₋ CF₃ Me H 3-CF₃₋₂₋ CF₃ pyridyl pyridyl Me H 3-Me-2- CF₃ Me H 3-Me-2- CF₃ pyridyl pyridyl Et H H OCF₃ Et H H OCF₃ Et H H C₂F₅ Et H H C₂F₅ Et H Me CF₃ Et H Me CF₃ Et H Me C₂F₅ Et H Me C₂F₅ i-Pr H Me CF₃ i-Pr H Me CF₃ Me Me H CF₃ Me H H CF₃ Me Me H OCF₃ Me H H OCF₃ Me Me H OCHF₂ Me H H OCHF₂ Me Me H C₂F₅ Me H H C₂F₅ Me Me H OCF₂CHF₂ Me H H OCF₂CHF₂ Me Me H SCF₂CHF₂ Me H H SCF₂CHF₂ Me Me H n-C₃F₇ Me H H n-C₃F₇ Me Me H i-C₃F₇ Me H H i-C₃F₇ Me Me H Br Me H H Br Me Me H Cl Me H H Cl Me Me H SCF₃ Me H H SCF₃ Me Me H CF₃ Me H Me CF₃ Me Me H OCF₃ Me H Me OCF₃ Me Me H OCHF₂ Me H Me OCHF₂ Me Me Me C₂F₅ Me H Me C₂F₅ Me Me Me OCF₂CHF₂ Me H Me OCF₂CHF₂ Me Me Me SCF₂CHF₂ Me H Me SCF₂CHF₂ Me Me Me n-C₃F₇ Me H Me n-C₃F₇ Me Me Me i-C₃F₇ Me H Me i-C₃F₇ Me Me Me Br Me H Me Br Me Me Me Cl Me H Me Cl Me Me Me SCF₃ Me H Me SCF₃ Me Me Me I Me H Me I Me Me Me SMe Me H Me SMe Me Me Me OMe Me H Me OMe Me Me Me OEt Me H Me OEt Me Me Me Et Me H Me Et Me Me Me SO₂Me Me H Me SO₂Me Me Me Me SO₂CF₃ Me H Me SO₂CF₃ Me Me Et CF₃ Me H Et CF₃ Me Me Et Br Me H Et Br Me Me Et Cl Me H Et Cl Me Me Ph CF₃ Me H Ph CF₃ Me Me Ph Br Me H Ph Br Me Me Ph Cl Me H Ph Cl Me Me 2-pyridyl CF₃ Me H 2-pyridyl CF₃ Me Me 2-pyridyl Cl Me H 2-pyridyl Cl Me Me 2-ClPh CF₃ Me H 2-ClPh CF₃ Me Me 2-ClPh OCF₃ Me H 2-ClPh OCF₃ Me Me 2-ClPh SCHF₂ Me H 2-ClPh SCHF₂ Me Me 2-ClPh Br Me H 2-ClPh Br Me Me 2-ClPh Cl Me H 2-ClPh Cl Me Me 3-Cl-2-pyridyl CF₃ Me H 3-Cl-2-pyridyl CF₃ Me Me 3-Cl-2-pyridyl OCF₃ Me H 3-Cl-2-pyridyl OCF₃ Me Me 3-Cl-2-pyridyl SCHF₂ Me H 3-Cl-2-pyridyl SCHF₂ Me Me 3-Cl-2-pyridyl Br Me H 3-Cl-2-pyridyl Br Me Me 3-Cl-2-pyridyl Cl Me H 3-Cl-2-pyridyl Cl Me Me 3-Br-2-pyridyl CF₃ Me H 3-Br-2-pyridyl CF₃ Me Me 3-Br-2-pyridyl OCF₃ Me H 3-Br-2-pyridyl OCF₃ Me Me 3-Br-2-pyridyl Br Me H 3-Br-2-pyridyl Br Me Me 3-Br-2-pyridyl Cl Me H 3-Br-2-pyridyl Cl Me Me CF₃ Me Me H CF₃ Me Me Me F CF₃ Me H F CF₃ Me Me Cl CF₃ Me H Cl CF₃ Me Me n-Pr CF₃ Me H n-Pr CF₃ Me Me i-Pr CF₃ Me H i-Pr CF₃ Me Me CF₃ CF₃ Me H CF₃ CF₃ Me Me OMe CF₃ Me H OMe CF₃ Me Me 2-BrPh CF₃ Me H 2-BrPh CF₃ Me Me 2-MePh CF₃ Me H 2-MePh CF₃ Me Me 2-CNPh CF₃ Me H 2-CNPh CF₃ Me Me 2-FPh CF₃ Me H 2-FPh CF₃ Me Me 2,6-F₂Ph CF₃ Me H 2,6-F₂Ph CF₃ Me Me 2,4-F₂Ph CF₃ Me H 2,4-F₂Ph CF₃ Me Me 2,5-F₂Ph CF₃ Me H 2,5-F₂Ph CF₃ Me Me 2-MeOPh CF₃ Me H 2-MeOPh CF₃ Me Me 3-F-2-pyridyl CF₃ Me H 3-F-2-pyridyl CF₃ Me Me 3-CF₃₋₂₋ CF₃ Me H 3-CF_(3-2..) CF₃ pyridyl pyridyl Me Me 3-Me-2- CF₃ Me H 3-Me-2- CF₃ pyridyl pyridyl Et Me H OCF₃ Et H H OCF₃ Et Me H C₂F₅ Et H H C₂F₅ Et Me Me CF₃ Et H Me CF₃ Et Me Me C₂F₅ Et H Me C₂F₅ i-Pr Me Me CF₃ i-Pr H Me CF₃ Me Cl H CF₃ Me Cl 2-ClPh CF₃ Me Cl H OCF₃ Me Cl 2-ClPh OCF₃ Me Cl H OCHF₂ Me Cl 2-ClPh SCHF₂ Me Cl H C₂F₅ Me Cl 2-ClPh Br Me Cl H OCF₂CHF₂ Me Cl 2-ClPh Cl Me Cl H SCF₂CHF₂ Me Cl 3-Cl-2-pyridyl CF₃ Me Cl H n-C₃F₇ Me Cl 3-Cl-2-pyridyl OCF₃ Me Cl H i-C₃F₇ Me Cl 3-Cl-2-pyridyl SCHF₂ Me Cl H Br Me Cl 3-Cl-2-pyridyl Br Me Cl H Cl Me Cl 3-Cl-2-pyridyl Cl Me Cl H SCF₃ Me Cl 3-Br-2-pyridyl CF₃ Me Cl Me CF₃ Me Cl 3-Br-2-pyridyl OCF₃ Me Cl Me OCF₃ Me Cl 3-Br-2-pyridyl Br Me Cl Me OCHF₂ Me Cl 3-Br-2-pyridyl Cl Me Cl Me C₂F₅ Me Cl CF₃ Me Me Cl Me OCF₂CHF₂ Me Cl F CF₃ Me Cl Me SCF₂CHF₂ Me Cl Cl CF₃ Me Cl Me n-C₃F₇ Me Cl n-Pr CF₃ Me Cl Me i-C₃F₇ Me Cl i-Pr CF₃ Me Cl Me Br Me Cl CF₃ CF₃ Me Cl Me Cl Me Cl OMe CF₃ Me Cl Me SCF₃ Me Cl 2-BrPh CF₃ Me Cl Me I Me Cl 2-MePh CF₃ Me Cl Me SMe Me Cl 2-CNPh CF₃ Me Cl Me OMe Me Cl 2-FPh CF₃ Me Cl Me OEt Me Cl 2,6-F₂Ph CF₃ Me Cl Me Et Me Cl 2,4-F₂Ph CF₃ Me Cl Me SO₂Me Me Cl 2,5-F₂Ph CF₃ Me Cl Me SO₂CF₃ Me Cl 2-MeOPh CF₃ Me Cl Et CF₃ Me Cl 3-F-2-pyridyl CF₃ Me Cl Et Br Me Cl 3-CF₃₋₂₋ CF₃ pyridyl Me Cl Et Cl Me Cl 3-Me-2- CF₃ pyridyl Me Cl Ph CF₃ Et Cl H OCF₃ Me Cl Ph Br Et Cl H C₂F₅ Me Cl Ph Cl Et Cl Me CF₃ Me Cl 2-pyridyl CF₃ Et Cl Me C₂F₅ Me Cl 2-pyridyl Cl i-Pr Cl Me CF₃

TABLE 14

R³ R⁴ R⁶ R^(5a) R^(5b) Me H Me H CF₃ Me H Me H OCF₃ Me H Me H OCHF₂ Me H Me H C₂F₅ Me H Me H OCF₂CHF₂ Me H Me H SCF₂CHF₂ Me H Me H n-C₃F₇ Me H Me H i-C₃F₇ Me H Me H Br Me H Me H Cl Me H Me H SCF₃ Me H Me Me CF₃ Me H Me Me OCF₃ Me H Me Me OCHF₂ Me H Me Me C₂F₅ Me H Me Me OCF₂CHF₂ Me H Me Me SCF₂CHF₂ Me H Me Me n-C₃F₇ Me H Me Me i-C₃F₇ Me H Me Me Br Me H Me Me Cl Me H Me Me SCF₃ Me H Me Me I Me H Me Me SMe Me H Me Me OMe Me H Me Me OEt Me H Me Me Et Me H Me Me SO₂Me Me H Me Me SO₂CF₃ Me H Me Et CF₃ Me H Me Et Br Me H Me Et Cl Me H Me Ph CF₃ Me H Me Ph Br Me H Me Ph Cl Me H Me 2-pyridyl CF₃ Me H Me 2-pyridyl Cl Me H Me 2-ClPh CF₃ Me H Me 2-ClPh OCF₃ Me H Me 2-ClPh SCHF₂ Me H Me 2-ClPh Br Me H Me 2-ClPh Cl Me H Me 3-Cl-2-pyridyl CF₃ Me H Me 3-Cl-2-pyridyl OCF₃ Me H Me 3-Cl-2-pyridyl SCHF₂ Me H Me 3-Cl-2-pyridyl Br Me H Me 3-Cl-2-pyridyl Cl Me H Me 3-Br-2-pyridyl CF₃ Me H Me 3-Br-2-pyridyl OCF₃ Me H Me 3-Br-2-pyridyl Br Me H Me 3-Br-2-pyridyl Cl Me H Me CF₃ Me Me H Me F CF₃ Me H Me Cl CF₃ Me H Me n-Pr CF₃ Me H Me i-Pr CF₃ Me H Me CF₃ CF₃ Me H Me OMe CF₃ Me H Me 2-BrPh CF₃ Me H Me 2-MePh CF₃ Me H Me 2-CNPh CF₃ Me H Me 2-FPh CF₃ Me H Me 2,6-F₂Ph CF₃ Me H Me 2,4-F₂Ph CF₃ Me H Me 2,5-F₂Ph CF₃ Me H Me 2-MeOPh CF₃ Me H Me 3-F-2-pyridyl CF₃ Me H Me 3-CF₃-2- CF₃ pyridyl Me H Me 3-Me-2- CF₃ pyridyl Et H Me H OCF₃ Et H Me H C₂F₅ Et H Me Me CF₃ Et H Me Me C₂F₅ i-Pr H Me Me CF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₂ Me Me H H C₂F₅ Me Me H H OCF₂CHF₂ Me Me H H SCF₂CHF₂ Me Me H H n-C₃F₇ Me Me H H i-C₃F₇ Me Me H H Br Me Me H H Cl Me Me H H SCF₃ Me Me H H CF₃ Me Me H H OCF₃ Me Me H H OCHF₃ Me Me H Me C₂F₅ Me Me H Me OCF₂CHF₂ Me Me H Me SCF₂CHF₂ Me Me H Me n-C₃F₇ Me Me H Me i-C₃F₇ Me Me H Me Br Me Me H Me Cl Me Me H Me SCF₃ Me Me H Me I Me Me H Me SMe Me Me H Me OMe Me Me H Me OEt Me Me H Me Et Me Me H Me SO₂Me Me Me H Me SO₂CF₃ Me Me H Et CF₃ Me Me H Et Br Me Me H Et Cl Me Me H Ph CF₃ Me Me H Ph Br Me Me H Ph Cl Me Me H 2-pyridyl CF₃ Me Me H 2-pyridyl Cl Me Me H 2-ClPh CF₃ Me Me H 2-ClPh OCF₃ Me Me H 2-ClPh SCHF₂ Me Me H 2-ClPh Br Me Me H 2-ClPh Cl Me Me H 3-Cl-2-pyridyl CF₃ Me Me H 3-Cl-2-pyridyl OCF_(3Me) Me Me H 3-Cl-2-pyridyl SCHF₂ Me Me H 3-Cl-2-pyridyl Br Me Me H 3-Cl-2-pyridyl Cl Me Me H 3-Br-2-pyridyl CF₃ Me Me H 3-Br-2-pyridyl OCF₃ Me Me H 3-Br-2-pyridyl Br Me Me H 3-Br-2-pyridyl Cl Me Me H CF₃ Me Me Me H F CF₃ Me Me H Cl CF₃ Me Me H n-Pr CF₃ Me Me H i-Pr CF₃ Me Me H CF₃ CF₃ Me Me H OMe CF₃ Me Me H 2-BrPh CF₃ Me Me H 2-MePh CF₃ Me Me H 2-CNPh CF₃ Me Me H 2-FPh CF₃ Me Me H 2,6-F₂Ph CF₃ Me Me H 2,4-F₂Ph CF₃ Me Me H 2,5-F₂Ph CF₃ Me Me H 2-MeOPh CF₃ Me Me H 3-F-2-pyridyl CF₃ Me Me H 3-CF₃-2- CF₃ pyridyl Me Me H 3-Me-2- CF₃ pyridyl Et Me H H OCF₃ Et Me H H C₂F₅ Et Me H Me CF₃ Et Me H Me C₂F₅ i-Pr Me H Me CF₃ Me Cl H H CF₃ Me Cl H H OCF₃ Me Cl H H OCHF₂ Me Cl H H C₂F₅ Me Cl H H OCF₂CHF₂ Me Cl H H SCF₂CHF₂ Me Cl H H n-C₃F₇ Me Cl H H i-C₃F₇ Me Cl H H Br Me Cl H H Cl Me Cl H H SCF₃ Me Cl H Me CF₃ Me Cl H Me OCF₃ Me Cl H Me OCHF₂ Me Cl H Me C₂F₅ Me Cl H Me OCF₂CHF₂ Me Cl H Me SCF₂CHF₂ Me Cl H Me n-C₃F₇ Me Cl H Me i-C₃F₇ Me Cl H Me Br Me Cl H Me Cl Me Cl H Me SCF₃ Me Cl H Me I Me Cl H Me SMe Me Cl H Me OMe Me Cl H Me OEt Me Cl H Me Et Me Cl H Me SO₂Me Me Cl H Me SO₂CF₃ Me Cl H Et CF₃ Me Cl H Et Br Me Cl H Et Cl Me Cl H Ph CF₃ Me Cl H Ph Br Me Cl H Ph Cl Me Cl H 2-pyridyl CF₃ Me Cl H 2-pyridyl Cl Me H H H CF₃ Me H H H OCF₃ Me H H H OCHF₂ Me H H H C₂F₅ Me H H H OCF₂CHF₂ Me H H H SCF₂CHF₂ Me H H H n-C₃F₇ Me H H H i-C₃F₇ Me H H H Br Me H H H Cl Me H H H SCF₃ Me H H Me CF₃ Me H H Me OCF₃ Me H H Me OCHF₂ Me H H Me C₂F₅ Me H H Me OCF₂CHF₂ Me H H Me SCF₂CHF₂ Me H H Me n-C₃F₇ Me H H Me i-C₃F₇ Me H H Me Br Me H H Me Cl Me H H Me SCF₃ Me H H Me I Me H H Me SMe Me H H Me OMe Me H H Me OEt Me H H Me Et Me H H Me SO₂Me Me H H Me SO₂CF₃ Me H H Et CF₃ Me H H Et Br Me H H Et Cl Me H H Ph CF₃ Me H H Ph Br Me H H Ph Cl Me H H 2-pyridyl CF₃ Me H H 2-pyridyl Cl Me H H 2-ClPh CF₃ Me H H 2-ClPh OCF₃ Me H H 2-ClPh SCHF₂ Me H H 2-ClPh Br Me H H 2-ClPh Cl Me H H 3-Cl-2-pyridyl CF₃ Me H H 3-Cl-2-pyridyl OCF₃ Me H H 3-Cl-2-pyridyl SCHF₂ Me H H 3-Cl-2-pyridyl Br Me H H 3-Cl-2-pyridyl Cl Me H H 3-Br-2-pyridyl CF₃ Me H H 3-Br-2-pyridyl OCF₃ Me H H 3-Br-2-pyridyl Br Me H H 3-Br-2-pyridyl Cl Me H H CF₃ Me Me H H F CF₃ Me H H Cl CF₃ Me H H n-Pr CF₃ Me H H i-Pr CF₃ Me H H CF₃ CF₃ Me H H OMe CF₃ Me H H 2-BrPh CF₃ Me H H 2-MePh CF₃ Me H H 2-CNPh CF₃ Me H H 2-FPh CF₃ Me H H 2,6-F₂Ph CF₃ Me H H 2,4-F₂Ph CF₃ Me H H 2,5-F₂Ph CF₃ Me H H 2-MeOPh CF₃ Me H H 3-F-2-pyridyl CF₃ Me H H 3-CF₃-2- CF₃ pyridyl Me H H 3-Me-2- CF₃ pyridyl Et H H H OCF₃ Et H H H C₂F₅ Et H H Me CF₃ Et H H Me C₂F₅ i-Pr H H Me CF₃ Me H Cl H CF₃ Me H Cl H OCF₃ Me H Cl H OCHF₂ Me H Cl H C₂F₅ Me H Cl H OCF₂CHF₂ Me H Cl H SCF₂CHF₂ Me H Cl H n-C₃F₇ Me H Cl H i-C₃F₇ Me H Cl H Br Me H Cl H Cl Me H Cl H SCF₃ Me H Cl Me CF₃ Me H Cl Me OCF₃ Me H Cl Me OCHF₂ Me H Cl Me C₂F₅ Me H Cl Me OCF₂CHF₂ Me H Cl Me SCF₂CHF₂ Me H Cl Me n-C₃F₇ Me H Cl Me i-C₃F₇ Me H Cl Me Br Me H Cl Me Cl Me H Cl Me SCF₃ Me H Cl Me I Me H Cl Me SMe Me H Cl Me OMe Me H Cl Me OEt Me H Cl Me Et Me H Cl Me SO₂Me Me H Cl Me SO₂CF₃ Me H Cl Et CF₃ Me H Cl Et Br Me H Cl Et Cl Me H Cl Ph CF₃ Me H Cl Ph Br Me H Cl Ph Cl Me H Cl 2-pyridyl CF₃ Me H Cl 2-pyridyl Cl Me H Cl 2-ClPh CF₃ Me H Cl 2-ClPh OCF₃ Me H Cl 2-ClPh SCHF₂ Me H Cl 2-ClPh Br Me H Cl 2-ClPh Cl Me H Cl 3-Cl-2-pyridyl CF₃ Me H Cl 3-Cl-2-pyridyl OCF₃ Me H Cl 3-Cl-2-pyridyl SCHF₂ Me H Cl 3-Cl-2-pyridyl Br Me H Cl 3-Cl-2-pyridyl Cl Me H Cl 3-Br-2-pyridyl CF₃ Me H Cl 3-Br-2-pyridyl OCF₃ Me H Cl 3-Br-2-pyridyl Br Me H Cl 3-Br-2-pyridyl Cl Me H Cl CF₃ Me Me H Cl F CF₃ Me H Cl Cl CF₃ Me H Cl n-Pr CF₃ Me H Cl i-Pr CF₃ Me H Cl CF₃ CF₃ Me H Cl OMe CF₃ Me H Cl 2-BrPh CF₃ Me H Cl 2-MePh CF₃ Me H Cl 2-CNPh CF₃ Me H Cl 2-FPh CF₃ Me H Cl 2,6-F₂Ph CF₃ Me H Cl 2,4-F₂Ph CF₃ Me H Cl 2,5-F₂Ph CF₃ Me H Cl 2-MeOPh CF₃ Me H Cl 3-F-2-pyridyl CF₃ Me H Cl 3-CF₃₋₂₋ CF₃ pyridyl Me H Cl 3-Me-2- CF₃ pyridyl Et H Cl H OCF₃ Et H Cl H C₂F₅ Et H Cl Me CF₃ Et H Cl Me C₂F₅ i-Pr H Cl Me CF₃ Me Cl H 2-ClPh CF₃ Me Cl H 2-ClPh OCF₃ Me Cl H 2-ClPh SCHF₂ Me Cl H 2-ClPh Br Me Cl H 2-ClPh Cl Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H 3-Cl-2-pyridyl OCF₃ Me Cl H 3-Cl-2-pyridyl SCHF₂ Me Cl H 3-Cl-2-pyridyl Br Me Cl H 3-Cl-2-pyridyl Cl Me Cl H 3-Cl-2-pyridyl CF₃ Me Cl H 3-Br-2-pyridyl OCF₃ Me Cl H 3-Br-2-pyridyl Br Me Cl H 3-Br-2-pyridyl Cl Me Cl H CF₃ Me Me Cl H F CF₃ Me Cl H Cl CF₃ Me Cl H n-Pr CF₃ Me Cl H i-Pr CF₃ Me Cl H CF₃ CF₃ Me Cl H OMe CF₃ Me Cl H 2-BrPh CF₃ Me Cl H 2-MePh CF₃ Me Cl H 2-CNPh CF₃ Me Cl H 2-FPh CF₃ Me Cl H 2,6-F₂Ph CF₃ Me Cl H 2,4-F₂Ph CF₃ Me Cl H 2,5-F₂Ph CF₃ Me Cl H 2-MeOPh CF₃ Me Cl H 3-F-2-pyridyl CF₃ Me Cl H 3-CF₃₋₂₋ CF₃ Me Cl H 3-Me-2- CF₃ Et Cl H H OCF₃ Et Cl H H C₂F₅ Et Cl H Me CF₃ Et Cl H Me C₂F₅ i-Pr Cl H Me CF₃ Formulation/Utility

Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight. Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water-soluble   5-90  0-94 1-15 Granules, Tablets and Powders. Suspensions, Emulsions, Solutions   5-50 40-95 0-15 (including Emulsifiable Concentrates) Dusts   1-25 70-99 0-5 Granules and Pellets 0.01-99  5-99.99 0-15 High Strength Compositions   90-99  0-10 0-2

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, N.Y., 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ.

Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, N.Y., 1963, pages 8-57 and following, and PCT Publication WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox-Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A.

Example A

Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether  2.0% sodium ligninsulfonate  4.0% sodium silicoaluminate  6.0% montmorillonite (calcined) 23.0%.

Example B

Granule Compound 1 10.0% attapulgite granules (low volatile matter, 90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

Example C

Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate  5.0% sodium alkylnaphthalenesulfonate  1.0% calcium/magnesium bentonite 59.0%.

Example D

Emulsifiable Concentrate Compound 1 20.0% blend of oil soluble sulfonates 10.0% and polyoxyethylene ethers isophorone 70.0%.

Example E

Granule Compound 1  0.5% cellulose  2.5% lactose  4.0% cornmeal 93.0%.

Compounds of this invention are characterized by favorable metabolic and/or soil residual patterns and exhibit activity controlling a spectrum of agronomic and non-agronomic invertebrate pests. (In the context of this disclosure “invertebrate pest control” means inhibition of invertebrate pest development (including mortality) that causes significant reduction in feeding or other injury or damage caused by the pest; related expressions are defined analogously.) As referred to in this disclosure, the term “invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests. The term “arthropod” includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term “gastropod” includes snails, slugs and other Stylommatophora. The term “nematode” includes all of the helminths, such as: roundworms, heartworms, and phytophagous nematodes (Nematoda), flukes (Tematoda), Acanthocephala, and tapeworms (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests. Compounds of this invention display activity against economically important agronomic, forest, greenhouse, nursery, ornamentals, food and fiber, public and animal health, domestic and commercial structure, household, and stored product pests. These include larvae of the order Lepidoptera, such as armyworms, cutworms, loopers, and heliothines in the family Noctuidae (e.g., fall armyworm (Spodoptera fugiperda J. E. Smith), beet armyworm (Spodoptera exigua Hübner), black cutworm (Agrotis epsilon Hufnagel), cabbage looper (Trichoplusia ni Hübner), tobacco budworm (Heliothis virescens Fabricius)); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers from the family Pyralidae (e.g., European corn borer (Ostrinia nubilalis Hübner), navel orangeworm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), sod webworm (Herpetogramma licarsisalis Walker)); leafrollers, budworms, seed worms, and fruit worms in the family Tortricidae (e.g., codling moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana Clemens), oriental fruit moth (Grapholita molesta Busck)); and many other economically important lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults of the order Blattodea including cockroaches from the families Blattellidae and Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella germanica Linnaeus), brownbanded cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea maderae Fabricius)); foliar feeding larvae and adults of the order Coleoptera including weevils from the families Anthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus)); flea beetles, cucumber beetles, rootworms, leaf beetles, potato beetles, and leaftniners in the family Chrysomelidae (e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), western corn rootworm (Diabrotica virgifera virgifera LeConte)); chafers and other beetles from the family Scaribaeidae (e.g., Japanese beetle (Popillia japonica Newman) and European chafer (Rhizoirogus majalis Razoumowsky)); carpet beetles from the family Dermestidae; wireworms from the family Elateridae; bark beetles from the family Scolytidae and flour beetles from the family Tenebrionidae. In addition it includes: adults and larvae of the order Dermaptera including earwigs from the family Forficulidae (e.g., European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches moria Fabricius)); adults and nymphs of the orders Hemiptera and Homoptera such as, plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers (e.g. Empoasca spp.) from the family Cicadellidae, planthoppers from the families Fulgoroidae and Delphacidae, treehoppers from the family Membracidae, psyllids from the family Psyllidae, whiteflies from the family Aleyrodidae, aphids from the family Aphididae, phylloxera from the family Phylloxeridae, mealybugs from the family Pseudococcidae, scales from the families Coccidae, Diaspididae and Margarodidae, lace bugs from the family Tingidae, stink bugs from the family Pentatomidae, cinch bugs (e.g., Blissus spp.) and other seed bugs from the family Lygaeidae, spittlebugs from the family Cercopidae squash bugs from the family Coreidae, and red bugs and cotton stainers from the family Pyrrhocoridae. Also included are adults and larvae of the order Acari (mites) such as spider mites and red mites in the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites in the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)), rust and bud mites in the family Eriophyidae and other foliar feeding mites and mites important in human and animal health, i.e. dust mites in the family Epidermoptidae, follicle mites in the family Demodicidae, grain mites in the family Glycyphagidae, ticks in the order Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus) and scab and itch mites in the families Psoroptidae, Pyemotidae, and Sarcoptidae; adults and immatures of the order Orthoptera including grasshoppers, locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locust (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket (Acheta domesticus Linnaeus), mole crickets (Gryllotalpa spp.)); adults and immatures of the order Diptera including leafrniners, midges, fruit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp., Phonnia spp.), and other muscoid fly pests, horse flies (e.g., Tabanus spp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sand flies, sciarids, and other Nematocera; adults and immatures of the order Thysanoptera including onion thrips (Thrips tabaci Lindeman) and other foliar feeding thrips; insect pests of the order Hymenoptera including ants (e.g., red carpenter ant (Camponotus ferrgineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsis geminata Fabricius), red imported fire ant (Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), crazy ant (Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus), cornfield ant (Lasius alienus Forster), odorous house ant (Tapinoma sessile Say)), bees (including carpenter bees), hornets, yellow jackets and wasps; insect pests of the order Isoptera including the eastern subterranean termite (Reticulitermes flavipes Kollar), western subterranean termite (Reticulitermes hesperus Banks), Formosan subterranean termite (Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder) and other termites of economic importance; insect pests of the order Thysanura such as silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard); insect pests of the order Mallophaga and including the head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch), dog biting louse (Trichodectes canis De Geer), fluff louse (Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus eurysternus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus) and other sucking and chewing parasitic lice that attack man and animals; insect pests of the order Siphonoptera including the oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephalides canis Curtis), hen flea (Ceratophyllus gallinae Schrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus) and other fleas afflicting mammals and birds. Additional arthropod pests covered include: spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes in the order Scutigeromorpha such as the house centipede (Scutigera coleoptrata Linnaeus). Activity also includes members of the Classes Nematoda, Cestoda, Trematoda, and Acanthocephala including economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida such as but not limited to economically important agricultural pests (i.e. root knot nematodes in the genus Meloidogyne, lesion nematodes in the genus Pratylenchus, stubby root nematodes in the genus Trichodorus, etc.) and animal and human health pests (i.e. all economically important flukes, tapeworms, and roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

Compounds of the invention show particularly high activity against pests in the order Lepidoptera (e.g., Alabama argillacea Hübner (cotton leaf worm), Archips argyrospila Walker (fluit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted bollworm), Helicoverpa armnigera Hübner (American bollworm), Helicoverpa zea Boddie (corn earworm), Heliothis virescens Fabricius (tobacco budworn), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis & Schiffermuiller (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hübner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperda J. E. Smith (fall armyworm), Trichoplusia ni Hübner (cabbage looper) and Tuta absoluta Meyrick (tomato leafiminer)). Compounds of the invention also have commercially significant activity on members from the order Homoptera including: Acyrthisiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potato aphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp. (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus Stål (rice leafhopper), Nilaparvata lugens Stål (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horvath (white-backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomaria McAtee white apple leafhopper, Erythroneoura spp. (grape leafhoppers); Magicidada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotus perniciosus Comstock (San Jose scale); Planococcus citri Risso (citrus mealybug); Pseudococcus spp. (other mealybug complex); Cacopsylla pyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmon psylla). These compounds also have activity on members from the order Hemiptera including: Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say (chinch bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schäffer (cotton stainer), Euchistus servus Say (brown stink bug), Euchistus variolarius Palisot de Beauvois (one-spotted stink bug), Graptosthetus spp. (complex of seed bugs), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper). Other insect orders controlled by compounds of the invention include Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthothnips citri Moulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip), and Thrips tabaci Lindeman (onion thrip); and the order Coleoptera (e.g., Leptinotarsa decemlineata Say (Colorado potato beetle), Epilachna varivestis Mulsant (Mexican bean beetle) and wireworms of the genera Agriotes, Athous or Limonius).

In accordance with this invention, compounds of Formula I, their N-oxides or salts thereof, and/or compounds of Formula II, their N-oxides or salts thereof, can be mixed with one or more other biologically active compounds or agents, e.g. a compound different from a compound of Formula I and/or Formula II and their N-oxides and salts, as the case may be, including insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural utility. Thus, compositions of the present invention comprising at least one Formula I compound and/or Formula II compound can also comprise at least one other biologically active compound or agent selected from the group consisting of an other insecticide, a fungicide, a nematocide, a bactericide, an acaricide, a growth regulator, a rooting stimulant, a chemosteilant, a semiochemical, a repellent, an attractant, a pheromone, a feeding stimulant, and an entomopathogenic bacterium, virus or fungus. Such compositions can further comprise at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.

Examples of other biologically active compounds or agents useful in this invention include: insecticides such as abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emnamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron; fungicides such as acibenzolar, azoxystrobin, benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, carpropamid, captafol, captan, carbendazirn, chloroneb, chlorothalonil, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole, (S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)4H-imidazol4-one (RP 407213), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil, flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin (SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis including ssp. aizawai and kurstaki, Bacillus thuringiensis delta eindotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

A general reference for these agricultural protectants is The Pesticide Manual, 12th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2000.

Of note are compositions which comprise at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent selected from the group consisting of abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

Preferred compositions include compositions which comprise at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent selected from the group consisting of a pyrethroid (e.g. cypermethrin, cyhalothrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin); a carbamate (e.g. fenothicarb, methomyl, oxamyl and thiodicarb); a neonicotinoid (e.g. clothianidin, imidacloprid and thiacloprid); a neuronal sodium channel blocker (e.g. indoxacarb); an insecticidal macrocyclic lactone (e.g. spinosad, abamectin, avermectin and emamectin); a waminobutyric acid (GABA) antagonist (e.g. endosulfan, ethiprole and fipronil); an insecticidal urea (e.g. flufenoxuron and triflumuron); a juvenile hormone mnimic (e.g. diofenolan and pyriproxyfen); pymetrozine; and amitraz. Preferred other biologically active agents useful in compositions of this invention include Bacillus thuringiensis and Bacillus thuringiensis delta endotoxin as well as naturally occurring and genetically modified viral insecticides including members of the family Baculoviridae as well as entomophagous fungi.

Of note are preferred compositions which comprise at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one biologically active compound or agent selected from the group consisting of cypermethrin, cyhalothrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate, tralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, clothianidin, imidacloprid, thiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin and entomophagous fungi.

Most preferred mixtures useful in the compositions and methods of this invention include a mixture of a compound of this invention with cyhalothrin; a mixture of a compound of this invention with cyfluthrin; a mixture of a compound of this invention with beta-cyfluthiin; a mixture of a compound of this invention with esfenvalerate; a mixture of a compound of this invention with methomyl; a mixture of a compound of this invention with imidacloprid; a mixture of a compound of this invention with thiacloprid; a mixture of a compound of this invention with indoxacarb; a mixture of a compound of this invention with abamectin; a mixture of a compound of this invention with endosulfan; a mixture of a compound of this invention with ethiprole; a mixture of a compound of this invention with fipronil; a mixture of a compound of this invention with flufenoxuron; a mixture of a compound of this invention with pyriproxyfen; a mixture of a compound of this invention with pymetrozine; a mixture of a compound of this invention with amitraz; a mixture of a compound of this invention with Bacillus thuringiensis and a mixture of a compound of this invention with Bacillus thuringiensis delta endotoxin.

In certain instances, combinations with other invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Thus, compositions and methods of the present invention can further comprise or utilize a biologically effective amount of at least one other invertebrate pest control compound or agent having a similar spectrum of control but a different mode of action from the compound of the invention. Contacting a plant genetically modified to express a plant protection compound (e.g., protein) or the locus of the plant with a biologically effective amount of a compound of this invention can also provide a broader spectrum of plant protection and be advantageous for resistance management.

At least one invertebrate pest is controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying, one or more of the compounds or compositions of this invention, in a biologically effective amount, to the environment of the pest including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pest to be controlled. Thus, the present invention further comprises a method for the control of at least one foliar- or soil-inhabiting invertebrate and/or protection of agronomic and/or nonagronomic environments, comprising contacting the invertebrate pest or its environment with a biologically effective amount of one or more of the compounds of the invention, or with a biologically effective amount of a composition comprising at least one such compound, or with a composition comprising at least one such compound and a biologically effective amount of at least biologically effective amount of a one other biologically active compound or agent. Examples of suitable compositions comprising at least one compound of the invention and at least one other biologically active compound or agent include granular compositions wherein the other biologically active compound is present on the same granule as the compound of the invention or on a granule that is separate from the granule where the compound of this invention is present.

A preferred method of contact is by spraying. Alternatively, a granular composition comprising a compound of the invention can be applied to the plant foliage or the soil. Compounds of this invention are effective in delivery through plant uptake by contacting the plant with a composition comprising a compound of this invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants. Other methods of contact include application of a compound or a composition of the invention by direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others.

The compounds of this invention can be incorporated into baits that are consumed by the invertebrates or within devices such as traps and the like. Granules or baits comprising between 0.01-5% active ingredient, 0.05-10% moisture retaining agent(s) and 40-99% vegetable flour are effective in controlling soil insects at very low application rates, particularly at doses of active ingredient that are lethal by ingestion rather than by direct contact.

The compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.

The rate of application required for effective control (i.e. “biologically effective amount”) will depend on such factors as the species of invertebrate to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.0001 kgthectare may be sufficient or as much as 8 kg/hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required. One skilled in the art can easily determine the biologically effective amount necessary for the desired level of invertebrate pest control.

The following Tests in the Biological Examples of the Invention demonstrate the control efficacy of compounds of this invention on specific pests. “Control efficacy” represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding. The pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-E for compound descriptions. The following abbreviations are used in the Index Tables that follow: t is tertiary, n is normal, i is iso, s is secondary, Me is methyl, Et is ethyl, Pr is propyl and Bu is butyl; accordingly i-Pr is isopropyl, s-Bu is secondary butyl, etc. Ac is COCH₃. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared. INDEX TABLE A

Compound R² R³ R⁴ R⁵ R⁶ m.p. ° C.  1 i-Pr H H 4-CF₃ H 200-202  2 Me H H 4-CF₃ H 198-200 (Ex. 1)  3 i-Pr H 5-Br 4-CF₃ H *  4 i-Pr H H 4-i-C₃F₇ H *  5 Me H H 4-i-C₃F₇ H 202-204 12 Et H 5-Cl 2-Me-4-CF₃ H 239-240 13 i-Pr H 5-Cl 2-Me-4-CF₃ H 238-239 14 Et H 6-Cl 2-Me-4-CF₃ H 228-230 15 i-Pr H H 2-Me-4-CF₃ Me 179-180 16 i-Pr H H 2-Me-4-OMe H 214-215 17 i-Pr H H 3-CF₃-5-CF₃ H 235-137 18 i-Pr H H 2,3-di-F H 237-238 19 i-Pr H H 2-Me-4-Cl H 216-217 20 Me H H 2-Me-4-CF₃ Me 218-219 21 Me H 6-Cl 2-Me-A-CF₃ H 225-226 22 i-Pr H H 2,3-di-Cl H 239-240 23 i-Pr H H 2,4-di-Cl H 209-210 24 i-Pr H H 2-Cl-4-CF₃ H 196-197 25 i-Pr H H 4-OCF₃ H 223-224 26 i-Pr H H 2-CF₃ H 241-242 27 i-Pr H H 2-Cl-4-CF₃ Me 189-190 28 Et H 5-Cl 2-Cl-4-CF₃ H 225-227 29 i-Pr H 5-Cl 2-Cl-4-CF₃ H 224-226 30 Me H 5-Cl 2-Cl-4-CF₃ H 245-247 31 i-Pr H 6-Cl 2-Me-4-CF₃ H 215-217 32 i-Pr H H 2-Me-4-Br H 212-213 33 Me H 6-Cl 2-Me-4-i-C₃F₇ H 213-214 *See Index Table D for NMR data.

INDEX TABLE B

Compound R² R³ R^(5a) R^(5b) m.p. ° C.  6 i-Pr H Me CF₃ 231-233  7 Me H Me CF₃ 261-263  8 Et H Me CF₃ 259-260  9 Me H Me i-C₃F₇ * 10 Et H Me i-C₃F₇ * 11 i-Pr H Me i-C₃F₇ * (Ex. 2)

INDEX TABLE C

Compound R² R³ R⁴ m.p. ° C. 34 i-Pr H H 74-75

INDEX TABLE D Cmpd No. ¹H NMR Data (CDCl₃ solution unless indicated otherwise)^(a) 3 δ 1.1(6H), 2.3(3H), 3.1(2H), 3.9(1H), 4.1(2H), 7.3(1H), 7.5(3H), 7.7(1H), 7.9(1H), 8.7(1H). 4 δ 1.14(d, 6H), 2.20(s, 3H), 3.13(t, 2H), 4.03-4.18(m, 1H), 4.25(t, 2H), 6.00(d, 1H), 6.95 (s, 1H), 7.14(t, 1H), 7.30-7.37(m, 2H), 7.40(d, 1H), 7.49(d, 1H), 8.20(d, 1H). 9 (DMSO-d₆) δ: 2.36(s, 3H), 2.59(d, 3H), 3.11(t, 2H), 4.00(t, 2H), 6.84(d, 1H), 6.99(t, 1H), 7.31(d, 1H), 7.42-7.48(m, 2H), 7.97(d, 1H), 9.39(s, 1H). 10 (DMSO-d₆) δ: 0.93(t, 3H), 2.37(s, 3H), 3.03(q, 2H), 3.13(t, 2H), 4.00(t, 2H), 6.98(t, 1H), 7.14(d, 1H), 7.33(d, 1H), 7.42-7.46 (m, 2H), 8.04(d, 1H), 9.29(s, 1H). 11 (DMSO-d₆) δ: 0.98(d, 6H), 2.37(s, 3H), 3.21(t, 2H), 3.62-3.71(m, 1H), 4.01(t, 1H), 6.73(d, 1H), 7.00(t, 1H), 7.32(d, 2H), 7.41-7.45(m, 2H), 8.14(d, 1H), 9.24(s, 1H). ^(a) ¹H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet, (bs q)-broad quartet.

BIOLOGICAL EXAMPLES OF THE INVENTION TEST A

For evaluating control of fall armyworm (Spodoptera frugiperda) the test unit consisted of a small open container with a 4-5-day-old corn (maize) plant inside. This was pre-infested with 10-15 1-day-old larvae on a piece of insect diet by use of a core sampler to remove a plug from a sheet of hardened insect diet having many larvae growing on it and transfer the plug containing larvae and diet to the test unit. The larvae moved onto the test plant as the diet plug dried out.

Test compounds were formulated using a solution containing 10% acetone, 90% water and 300 ppm X-77®Spreader Lo-Foam Formula non-ionic surfactant containing alkylarylpolyoxyethylene, free fatty acids, glycols and isopropanol (Loveland Industries, Inc. Greeley, Colo., USA), unless otherwise indicated. The formulated compounds were applied in 1 mL of liquid through a SUJ2 atomizer nozzle with 1/8 JJ custom body (Spraying Systems Co. Wheaton, Ill., USA) positioned 1.27 cm (0.5 inches) above the top of each test unit. All experimental compounds in this screen were sprayed at 50 ppm and replicated three times. After spraying of the formulated test compound, each test unit was allowed to dry for 1 hour and then a black, screened cap was placed on top. The test units were held for 6 days in a growth chamber at 25° C. and 70% relative humidity. Plant feeding damage was then visually assessed.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1, 2, 4, 5, 21 and 33.

TEST B

For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of a small open container with a 6-7 day old cotton plant inside. This was pre-infested with 8 2-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 50 ppm as described for Test A. The applications were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1 and 2.

TEST C

For evaluating control of diamondback moth (Plutella xylostella) the test unit consisted of a small open container with a 12-14-day-old radish plant inside. This was pre-infested with 10-15 neonate larvae on a piece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 50 ppm as described for Test A. The applications were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1, 2, 4, 5, 21, 25 and 33.

TEST D

For evaluating control of beet armyworm (Spodoptera exigua) the test unit consisted of a small open container with a 4-5-day-old corn plant inside. This was pre-infested with 10-15 1-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 50 ppm as described for Test A. The applications were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 4. 

1. A method for controlling at least one invertebrate pest, comprising: contacting the invertebrate pest or its environment with a biologically effective amount of at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof

wherein each J is independently a phenyl ring or a 5- or 6-membered heteroaromatic ring, each ring substituted with 1 to 4 R⁵; A and B are independently O or S; n is 0, 1, 2 or 3; R¹ is H, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl or C₃-C8 dialkylaminocarbonyl; or R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; R³ is H; or R³ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl and C₁-C₄ alkylsulfonyl; or R² and R³ can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy; and each R⁴ and each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, or C₃-C₆ trialkylsilyl; or each R⁴ and each R⁵ is independently a phenyl, benzyl, phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or two R⁵ groups when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—; M and M¹ are each independently CR⁶R⁷, NR⁸, O or S when the bond between M and M¹ is a single bond; and are each independently CR⁶ or N when the bond between M and M¹ is an aromatic bond; each R⁶ and each R⁷ is independently H, C₁-C₄ alkyl, halogen, CN, C₁-C₄ haloalkyl or C₁-C₄ alkoxy; and each R⁸ is independently H or C₁-C₄ alkyl.
 2. The method of claim 1 comprising applying a biologically effective amount of a compound of Formula I wherein A and B are both O; R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and n is 0, 1 or
 2. 3. The method of claim 1 comprising applying a biologically effective amount of a compound of Formula II wherein A and B are both O; R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and n is 0, 1 or
 2. 4. A composition comprising: at least one compound selected from the group consisting of a compound of Formula I as defined in claim 1, an N-oxide or a salt thereof, and a compound of Formula II as defined in claim 1, an N-oxide or a salt thereof; and at least one other biologically active compound or agent.
 5. The composition of claim 4 further comprising an additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.
 6. The composition of claim 4 wherein the other biologically active compound or agent is selected from the group consisting of an other insecticide, a fulngicide, a nematocide, a bactericide, an acaricide, a growth regulator, a rooting stimulant, a chemosterilant, a semiochemical, a repellent, an attractant, a pheromone, a feeding stimulant, and a entomopathogenic bacterium, virus or fungus.
 7. The composition of claim 6 wherein the other insecticide is selected from the group consisting of a pyrethroid, a carbanate, a neonicotinoid, a neuronal sodium channel blocker, an insecticidal macrocyclic lactone, a yaminobutyric acid (GABA) antagonist, an insecticidal urea, a juvenile hormone mimic, pymetrozine, and amitraz.
 8. The composition of claim 6 wherein the other insecticide is selected from the group consisting of abarnectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethiin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, suiprofos, tebufenozide, teflubenzuron, tefluthin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
 9. The composition of claim 6 wherein the other insecticide is selected from the group consisting of cypermethrin, cyhalothrin, cyfluthrin, beta-cyfluthrn, esfenvalerate, fenvalerate, tralomethrn, fenothicarb, methomyl, oxamyl, thiodicarb, clothianidin, imidacloprid, thiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin and entomophagous fungi.
 10. A method for controlling at least one invertebrate pest, comprising: contacting the invertebrate pest or its environment with a biologically effective amount of a composition of claim 4 or claim
 5. 11. A compound of Formula II as defined in claim 1, an N-oxide thereof or a salt thereof.
 12. The compound of claim 11 wherein A and B are both O; R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and n is 0, 1 or
 2. 13. The compound of claim 12 wherein J is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4, each J ring optionally substituted with 1 to 3 R⁵

Q is O, S or NR⁵; W, X, Y and Z are independently N or CR⁵, provided that in J-3 and J4 at least one of the group consisting of W, X, Y and Z is N; R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; R³ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl; each R⁴ is independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl; each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₆ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl; or each R⁵ is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or two R⁵ groups when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—.
 14. The compound of claim 13 wherein R² is H; R³ is C₁-C₄ alkyl; and at least one R⁵ is other than H and is attached to J at the position ortho to the N(R¹)C(═B) moiety.
 15. A composition comprising: at least one compound of claim 11; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent.
 16. A method for controlling at least one invertebrate pest, comprising: contacting the invertebrate pest or its environment with a biologically effective amount of a compound of claim 11 or with a biologically effective amount of a composition of claim
 15. 17. A compound of Formula Id, an N-oxide or a salt thereof,

wherein each J is independently a phenyl ring or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with 1 to 4 R⁵; A and B are independently O or S; n is 0, 1, 2 or 3; R¹ is H, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl; or R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; R³ is H; or R³ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl and C₁-C₄ alkylsulfonyl; or R² and R³ can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy; and each R⁴ and each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, or C₃-C₆ trialkylsilyl; or each R⁵ is independently a phenyl, benzyl, phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylanino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or two R⁵ groups when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—; M and M¹ are each independently CR⁶R⁷, NR⁸, O or S when the bond between M and M¹ is a single bond; and are each independently CR⁶ or N when the bond between M and M¹ is an aromatic bond; each R⁶ and each R⁷ is independently H, C₁-C₄ alkyl, halogen, CN, C₁-C₄ haloalkyl or C₁-C₄ alkoxy; and each R⁸ is independently H or C₁-C₄ alkyl.
 18. The compound of claim 17 wherein A and B are both O; R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; and n is 0, 1 or
 2. 19. The compound of claim 18 wherein J is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4

Q is O, S or NR⁵; W, X, Y and Z are independently N or CR⁵, provided that in J-3 and J-4 at least one of the group consisting of W, X, Y and Z is N; R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; R³ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl; each R⁴ is independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl; each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₆ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl; or each R⁵ is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; or two R⁵ groups when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—.
 20. The compound of claim 19 wherein R¹ is H or C₁-C₄ alkyl; R² is H or C₁-C₄ alkyl; R³ is H, C₁-C₄ alkyl optionally substituted with halogen, CN, OCH₃, or S(O)_(p)CH₃; each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₂-C₄ alkoxycarbonyl or C₃-C₈ dialkylaminocarbonyl; or a phenyl, benzyl, or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with halogen, CN, NO₂, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy, provided that at least one R⁵ is other than H and is attached to J at the position ortho to the N(R¹)C(═B) moiety; and p is 0, 1 or
 2. 21. The compound of claim 20 wherein J is a substituted phenyl, a substituted pyrazole, a substituted pyrrole, a substituted pyridine or a substituted pyrimidine.
 22. The compound of claim 21 wherein R¹ and R² are each H.
 23. A composition comprising: at least one compound of claim 17; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent.
 24. A method for controlling at least one invertebrate pest, comprising: contacting the invertebrate pest or its environment with a biologically effective amount of a compound of claim 17 or with a biologically effective amount of a composition of claim
 23. 